


Frat Boy

by SupernaturalWinchester67



Series: Frat Boy [1]
Category: Supernatural
Genre: Alternate Universe - College/University, Anal Plug, Anal Sex, Bets & Wagers, Blindfolds, Blow Jobs, Breathplay, College Student Dean Winchester, Daddy Kink, Eventual Relationships, Eventual Romance, F/M, Falling In Love, Family Feels, Fluff, Hand Jobs, Impala Sex, Kissing, Light Bondage, Light Dom/sub, Multiple Orgasms, Oral Sex, Orgasm Denial, Roleplay, Romance, Semi-Public Sex, Sex, Smut, Student Reader, Vaginal Fingering
Language: English
Status: Completed
Published: 2018-12-06
Updated: 2018-12-06
Packaged: 2019-09-12 12:22:14
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 22
Words: 76,541
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16872822
Author URL: https://archiveofourown.org/users/SupernaturalWinchester67/pseuds/SupernaturalWinchester67
Summary: The reader goes to a Frat party and meets cocky Frat boy Dean Winchester. Loaded with fluff, sex and feels, Dean and the reader embark on a relationship neither one of them could of predicted…





	1. Chapter 1

You’d left your friends who were beyond drunk in the very capable hands of one of their boyfriends. The average one. Or maybe it was the tall one…you didn’t know. You weren’t on babysitting duty tonight and that was good enough for you. 

The kitchen was surprisingly sparse as you cut through the back door to open one of several coolers filled with beer on the patio. As you leaned over to grab one, you heard a loud whistle. Instead of glaring at him like you might in the light of day, you moved your hips forward as you stood up, giving him just the smallest hint of what you were capable of.

“Like the show?” you said with a smirk as you turned to face him. Seeing him for the first time you couldn’t help but lose a little of your drunken confidence. He looked  _good_. 

“You leave your mouth open like that you might catch something more than flies,” he said with a wink, stepping towards you. You closed your jaw, not realizing you’d dropped it in the first place. 

“Yeah, well…” you said, stepping past him to return to the party. You heard another whistle that made you pause.

“Honey, you gotta stop showing me that backside of yours,” he said as you turned to look at him. “Don’t compare to the front though,” he said, just barely licking his lips. You bit down on yours as you watched his tongue move methodically slow. 

“Thanks for the compliant, frat boy,” you said, waving your beer at him and returning inside. 

An hour later you’d hit that sweet spot. You were drunk but didn’t feel sick. You had energy for days and were far more ballsy than your normal state. You went to use the bathroom and when you left, you saw him standing right outside. You looked him up and down like you’d just won him as a prize.

The boots told you he wasn’t one of the stuck up trust fund kids. His dark jeans, black t-shirt and blue flannel were simple but fit him so well it was if he was wearing a tux. His face, that strong jaw, those jaded eyes,  _the hair_. Damn hair like that was your weakness.

“So how’s my front?” he asked, crossing his arms in front of himself, showing off his muscles. You bet he was gorgeous underneath all those clothes. His words snapped you out of your haze. “Or is my backside more your thing?” 

He spun around slowly, giving you a small glimmer of his toned back before facing you again.

“Um…what?” you asked, a little haze surrounding you. He approached you, caging you between his arms as your back hit the wall in the secluded hallway.

“Well we already established that while I enjoy every angle of that hot body, I like your front best. What side of me do you like sweetheart? I can put on another routine for you if you’d like,” he said, his breath hot. 

Everything in you told you he was a stupid frat boy looking for a hookup. God, you’d even started referring to him as frat boy in your head. But he was just…

“Wanna play some pool?” he asked, dropping his arms but staring down at you with lustful eyes. You nodded and followed him to a room with little more than empty beer bottles and an old pool table. Frat boy waved off the two of his fellow brothers that were playing. The tallest one, he was taller than frat boy even, whispered in your ear as he walked out.

“Have fun,” he said. You knew you weren’t that drunk and just looked at the guy until he walked out. 

“What was that about?” you asked while frat boy set up the balls but he just shrugged. You smiled. “Is this some sort of foreshadowing?” you said, pointing at them as he rolled over the top of them with his hands. He laughed.

“Sweetheart’s not so sweet is she?” he said, handing you a cue, green eyes locking onto yours. His pupils were dilated ever so slightly and you knew he was turned on.

“Sorry frat boy, I’m not that easy,” you said with a wink. He smiled and glanced down before looking back and smiling again.

“Maybe you’re not that easy,” he said, striking the cue ball and scattering the balls across the table. None of them went in. “But I know what you want,” he said, hands rubbing up and down the pool cue.

“You want to give me a hand job, frat boy?” you said. He merely raised his eyebrows and tilted his head away before looking back mischievously. 

“Well, I believe in everyone having a good time so if you want a hand job, who am I to deny you?” he said. You chuckled and walked around the other side of the table, ready to start playing.

“You’re gonna have to offer something better than that if you want me, frat boy,” you said. 

“Dean,” he said. You stopped lining up your shot and let your eyes roam over him. He was definitely a Dean.

“Y/N,” you said, causing Dean to smile. He moved around the table to where you were before you could pull your arm back.

“Want to make this interesting?” he asked, his fingers lightly touching the top of your hand, sending sparks in you. You knew he’d played this game before. That didn’t mean it wasn’t a game you wanted to play. 

“Go on,” you said, turning and popping your hip out. 

“Simple really. You win, I’ll get you the orgasm you’re looking for and your pretty little lips won’t even have to be introduced to my cock,” he said, raising his hands, your eyes wandering down for a moment. 

“And if you win?” you asked, relishing in the idea of possibly losing just to get to suck him for everything he was worth. Dean gave you a wicked smile.

“Give me a number,” he said, walking back to the other side of the table.

“A what?” you asked.

“How many times do you want me to make you cum?” he asked you. You were taken aback at the question.

“I don’t…”

“How about we break my old record?” he said. You could feel yourself getting wet right there, your pussy tightening at the thought.

“What’s your-”

“Ah ah,” he said wagging his finger. “Deal?” he said, holding his hand across the table. You didn’t hesitate in the slightest to shake it. 

Dean licked his lips one more time before grabbing his pool cue. “This is going to be fun,” he said, lining up and taking a shot.

Fifteen minutes later you were leaning against the wall. Dean was a fucking con man in your opinion. You hadn’t even played yet and he only had one ball left. It didn’t take long for him to sink it.

“I know, this seems a little unfair,” he said, taking the unused cue from your hand, his eyes a darker shade of green. “But did you really want to win, Y/N?” he asked, placing them on the table. You took a deep breath. Dean nodded and laughed to himself. “That’s what I thought. Now come on, frat boy’s got a record to break sweetheart,” he said, reaching for your hand and pulling you out of the room.

You let Dean drag you through the crowded front room and to the base of the stairs when he pulled you in quick, pressing your chest against his.

“You do want this right?” he said into your ear over the roar of the music. You reached your free hand to grab him by the belt and tugged roughly. Dean looked ready to devour you right there but managed to keep his composure. He ran with you up the stairs and then up another flight to the third floor.

It was quieter up here, seemingly abandoned. Dean led you towards the room at the end of the hall, letting go of you just long enough to unlock his door. He grabbed you by the waist and pulled you into the dimly lit room. Dean kicked the door shut with his foot, locking it again with his free hand.

“Cleaner than I thought frat boy,” you said looking around the room. Dean’s lips were on your neck, nipping at the skin and you tilted your head to give him better access. You felt him dig into it, leaving marks on your body. Your core was tightening even further when Dean’s left hand began to unbutton your jeans, his right keeping you tight against him.

“I bet you’re soaked already,” he mumbled against your skin, his teeth grazing your earlobe. You moved your hands over your head, resting them on top of Dean’s head. You tugged on his hair and felt him jerk back. “You want it rough, little girl?” he said, lips brushing against your ear, his breath warm and needy.

You kept your right hand in his hair and slid your left down behind you, finding his jeans and trying to work him out of them. Dean had unbuttoned your pants, his fingers playing with the elastic of your underwear, begging to dive beneath.

“I said do you want it rough,” he said, power in his voice. You shifted your legs to gain some desperately needed friction.

“I don’t know, is frat boy even capable of doing that? I’m afraid your talk might be the only thing cocky about you,” you said, pulling away from him and looking at him through your lashes. Dean took a deep breath as you laughed and backed away towards his bed. “You think you can make me cum?”

“I know I can make you cum, make you scream my name until I fuck you so hard you won’t be able to walk straight,” he said, advancing on you like a predator. You crossed your arms and gave him the same smirk he gave you after he’d won.

“You really think you can fuck my pussy that good?” you said, standing your ground at the foot of his bed. Even in the poor light, you could see his pupils were blown, his bulge getting tighter in his pants. You expected a comeback but Dean only stood in front of you, eyes boring into yours. He lifted the bottom of your shirt and you watched as he pulled your jeans down just a little to give him some room to work. His lips devoured yours, both of you fighting for control with your tongues, the taste of whiskey on his mouth. You felt a finger graze your skin before slipping under the fabric and making it’s way down your mound. 

A moan escaped your mouth and was swallowed by Dean as his finger discovered your clit and began rubbing in slow circles. He didn’t go slow for long though, quickly bringing up his speed and pressure so that it felt like bolts of lightening were coursing through you. He was demanding and you gave in to letting him have his way with your mouth, trying your best to keep your shaking knees upright. You let another wanton moan out as you felt your high building within you.

“God Dean, oh fucking shit,” you said, your hands wrapped tightly in his shirt trying to hold on. You closed your eyes. You wanted rough but never imagined he’d live up to his word.

“Go ahead and cum. Now,” he ordered and your body obeyed, Dean’s finger pushing against your clit and intensifying the feeling. You began to yell out as he kissed you again, occupying you through your orgasm. Eventually he pulled away and you took in a deep breath, trying to get some air back in your lungs.

“Oh fuck oh fuck oh fuck,” you got out as you felt Dean’s finger suddenly invade your pussy, thrusting in deep at at rapid pace. “I can’t-” you got out, Dean’s palm rubbing against your sensitive clit.

“Fuck little girl, don’t make bet’s you can’t live up to,” he said, adding a second finger between thrusts, a groan ripping from your throat. “Just wait til it’s my cock. I can’t wait to fuck that pretty face, fuck that pussy,” he said as his fingers continued to ravish you at a maddening pace.

“Dean,” you said, your voice so needy. You’d never sounded that needy before. But you felt so sensitive, every little touch set you on fire, every pound of his fingers inside of you, hitting your G-spot with every movement. You felt him add a third finger, and your body was trembling now, Dean’s free hand keeping you upright. “Please Dean,” you begged, your release close.

“Everytime you see me, everytime you even think of me, that pussy’s gonna be so wet. No one’s ever going to fuck you as good as me,” he said, his fingers curling inside you. 

You cry out as you clench around him, his fingers never stopping. “Dean! Fuck Dean! So fucking good,” you scream, dropping your head against his shoulders, looking down to see him fucking you with his fingers. 

Suddenly he pulls them from you and tastes them, a smile on his face. “Damn, you’re delicious,” he said, moving in to kiss you. Your juices mixed with the lingering alcohol on his breath drives you wild as Dean pulls your jeans off without breaking his lips from yours. 

“Now…” he said, backing away, undoing his belt. “My turn,” he said, dropping his pants in one quick motion. You let out a small moan at the sight of him and hated it. Frat boy had you fucking hooked before you even had his cock. Now it was all you wanted. “Strip,” he said and you lost the rest of your clothes in seconds. Dean removed his shirt and you decided if you were going to hell for this, it was more than worth the punishment.

“Knees,” he said and you dropped so hard and fast you were sure the party-goers two floors down heard. He walked over to you, letting you admire him as you licked your lips in want, unsure of how on earth you would take him all. His tip was red and leaking precum, the salty concoction smeared across it. He was rock hard, longer than you could have hoped for, thicker than you could have dreamed of. You heard him laugh when you realized you’d only been staring at his cock.

“Little girl likes my cock I think,” he said, brining the tip dangerously close to your mouth. You leaned forward to take him in but he stepped back. “Fingers,” he said. “You want this, you gotta fuck yourself at the same time,” he said. 

You plunged three fingers into yourself and began to pump them in and out, looking up at Dean as you kneeled on the floor.

“Fuck,” you said, your fingers fighting to push past the hesitancy your body was having at the thought of another orgasm. It didn’t last long and you felt the slow build of the pressure begin again.

“Want me to fuck that mouth of yours now?” asked Dean. You nodded your head eagerly as the sounds of your fingers moving in and out filled the room. How he hadn’t fucked himself yet you had no idea.

“Please, want to suck that cock, let you fuck my face,” you said, increasing the speed of your fingers slightly. Dean gave you a wicked grin again as he approached you and stopped, his cock an inch from your face.

“Suck,” he said and your lips were on him in an instant. You wanted to take him all at once but wanted to torture him a little too. You licked the precum off of his tip, the taste heavenly as the salt hit your tongue. You gave him small kisses up and down his shaft when you felt a rough hand in your hair. You looked up and saw that Dean was done playing.

You let him guide your mouth as your lips wrapped around his cock, slowly taking more and more of him until his tip hit the back of your throat. You wanted to gag but you wanted to take all of him. You kept going until your lips hit Dean’s base, your air cut off. You both settled for a moment as you felt his cock twitch inside you and down your throat.

“Fuck little girl, knew you were fucking good. No one’s ever been able to do that before,” he said, a moan in his words.

You pulled him off slowly, leaving a long lick on his underside and hollowing your cheeks as you did so. Your lips left him with a ‘pop’ as you took a deep breath. 

“Ready frat boy?” you said, licking your lips before you leaned back in. Dean’s hand in your hair held you back.

“Fingers sweetheart,” he said, looking down to where your hand had stopped moving in and out of yourself. You hadn’t even realized you’d done so, so focused on trying to suck all of him. You started pumping again, giving yourself a rough pace knowing it would make Dean happy. He rewarded you by letting you pull close to his tip, taking him in your mouth again.

Your legs burned as your body shook, from your own pleasure or the sounds you were eliciting from Dean you weren’t sure. His hand in your hair helped you move faster and harder over his length, every throb and twitch of his cock felt on your tongue and throat.

“I’m g-gonna…” Dean stuttered out. Your hand was sore but your end was so close you thrust harder and harder into yourself, bobbing up and down Dean as he fucked your face. 

You felt your walls clamp down on your fingers harder than you’d ever done before, a scream erupting in your throat as you moaned around Dean.

“Y/N! Fuck!” he yelled as his cock throbbed and you felt his cum hit the back of your throat and fill your mouth. You swallowed as he continued to shoot stream after stream into you before finally pulling off of you. His taste was glorious as you took down the rest that had pooled in your mouth, a little dribbling down your chin as he removed his cock.

You removed your fingers and fell to the floor exhausted, your knees unable to stay upright. You panted heavily as a strong hand grabbed you by the jaw and forced your head up. Dean kneeled in front of you, eyes looking into yours as he used his thumb to wipe away the leftover cum. You stuck out your tongue to suck it off but he tasted himself before you had the chance. You pouted at the loss.

“Don’t worry sweetheart,” said Dean between breaths, “I’m not done with you yet,” he said, grabbing you by the waist and pulling you onto the bed.

“Dean, I need a second,” you said, your chest heaving. Dean reached out with a hand as he climbed over you, using one hand to hold himself as he used the other to knead your breast.

“Take a break little girl, let me do all the work,” he said, his fingers rolling and squeezing your nipple roughly. You arched your back into him, the pleasure shooting straight to your core. Dean kissed you as he played with one breast and then the other, giving them both attention, giving you a chance to come down from your high.

“No no little girl,” he said as you fluttered your eyes closed, sleepiness overcoming you. You opened them again to see him reach his hand down to line himself up with your entrance, a moan escaping your lips at the thought. “Now what do you want me to do to this tight little cunt?”

“Fuck me,” you said, reaching for him. Dean used his free hand to grab your wrists.

“Just fuck you?” he said, cockiness radiating off of him.

“Fuck my pussy, fuck me so hard I scream your name,” you said, need in your voice once more. With that Dean thrust into you in one swift motion. “Dean!” you yelled out. His cock felt even bigger now that it was buried tight within you. He was so deep, pressed in as far as he could go as he stilled for a moment, watching you writhe beneath him at the feeling. His hands released yours and you pulled him close.

“Love the way you take my cock, that little pussy feels so good,” he said, pulling back, leaving just his tip in you before thrusting in all the way again. You let out another moan as Dean groaned deeply. 

“Please,” you said as your pussy ached with need, the promise of another orgasm building up again. “Fuck me, fuck me so hard,” you whined, your hands running down his chest. Dean smiled and pulled out quicker and thrust in harder than before. 

His pace was relentless, only increasing with speed as he went. It felt as though he would tear through you as your orgasm built up faster than ever before. You knew it was going to be big, Dean’s powerful thrusts, his hands pining your hips to the bed, you were on the edge longer than you’d ever been before and it was amazing.

“D-Dean…” you got out as you clamped down hard on him, your fourth orgasm hitting you like a tidal wave. His name was the only thing you could scream out, the only thing you could think of. God you couldn’t think of anything anymore except for him.

“Love the way you feel, love how tight that little cunt is,” he said, slowing his thrusts to let you come down from your body racking orgasm. “Congratulations are in order, Y/N,” he said, his slow thrusts continuing, another orgasm prepping itself.

“Dean,” you got out, your hands all over him, all over you. Every little touch from him built you up, sent you closer to that edge. In a matter of seconds you were cuming again.

“Didn’t even mean to do that one, sweetheart,” he said, his thrusts never stopping as you rode out the orgasm. “I was going to tell you that you tied the record but I think you just broke it,” he said, his thrusts increasing in strength. “Tell me what you want,” he said, fingers digging into your skin, sure to leave bruises.

“Fuck my pussy, fill up my tight cunt with your cum, make me cum around that huge fuckin’ cock,” you said, grabbing his ass so he would hit you deeper. 

“God you’re fucking perfect,” said Dean, his hips pumping into you faster, causing you to arch your head back. Your cries of pleasure and Dean’s sweet moans and grunts filled the room, the slap of sweaty skin on skin loud in your ears. “So fuckin’ perfect,” said Dean, his cock throbbing within in you. 

“I’m gonna…” you got out as you felt the crest of your orgasm start to hit you.

“Y/N!” cried out Dean, his cum splashing your walls, sending your orgasm higher than before. You screamed as you locked down on his twitching cock, your walls squeezing every drop of cum from he had to offer. It felt like your orgasm lasted forever before you finally felt yourself come down. The look on Dean’s face told you he felt the same way.

Finally Dean pulled out of you, some of his cum dripping out of your pussy. Dean thrust three fingers in and curled them, bringing them out again. He brought them to your lips where you found a collection of his cum on his fingers and you eagerly sucked them clean. Dean thrust in a few more times and let you taste him before swilring his fingers around you one last time, ensuring he’d gotten all he could from you.

Dean lay back on the bed, face close to yours. You were spent and all you could think of was him. He gave you one last rough kiss before pulling away and rolling off the bed.

“Six huh?” he said. “You’re the new champ sweetheart. In record time I might add,” he said, walking over to where his clothes lay on the ground. He tossed you yours before stepping into his boxers. “Come on, we’ve got a party to get back to,” he said with a wink.

 

“Hiya sweetheart,” you heard from behind you as you read over some of your notes on a bench. It’d been three days since you heard that voice and it brought a smile to your lips. You turned your head to see a familiar face walking to face you head on. 

“Frat boy,” you said, tilting your head and nodding. He even looked sexy wearing a backpack. He shoved his hands in his pockets and rocked on his heels as he gave you a confident smile.

“We’ve got another party on saturday if you want to, ya know…come,” he said placing emphasis on the last word. His eyes were more than confident as they gazed down to see you squeeze your legs together. He broke away to look up at the cloudy sky overhead and back at you. “You feel wet?” he asked as you swallowed a gulp. He was right. As soon as you saw him, heard that masculine voice, you felt yourself begin to drip. “Thought I felt rain,” he said as another student nearby passed you. “So party saturday?” he asked.

“Wanna make a bet?” you said, looking back at your notes. Dean laughed. 

“A bet with you? This’ll be good,” he said, excitement in his voice. You turned to look up at him.

“I get the number 1, you get the number 2. We go ask five random people on the quad to choose either one or the other. Whoever gets more of their number wins,” you said, closing your notebook. Dean smiled.

“Okay, simple but I like it. Stakes?” he said, crossing his arms. You gave him the wicked grin he’d so often given you that night.

“You win, saturday night I’m yours. You want to break our record, try my back door, whatever you want, no objections,” you said. Dean’s smile only grew.

“I think I can work with that. If you win?” he asked. You stood up from your seat and got right in his face.

“Two weeks. I want you, I get you. Day or night, my place or yours…and I make the rules,” you said. Dean pondered over your words for a moment.

“New stakes. I get to do whatever I want, no questions asked,” he said. You knew he’d take advantage of you but he’d ask permission first and that was enough for you. “And I get you for a  _month_ ,” he said, lips just inches from yours.

“Winner gets  _whatever_  they want,  _whenever_  they want for a month,” you said, sticking out your hand. Dean shook it eagerly before dropping it and heading over towards a group of students laying on the nearby grass.

“Ready to play sweetheart?” he said, beckoning you over to him. 

“Game on, frat boy,” you said with a smile.


	2. Chapter 2

**Summary for the Chapter:**

> Dean and reader find out who wins their little bet…

“Fuck,” you growled under your breath as you and Dean walked away from the fifth person in your little game. You didn’t want to look at him, see that cocky smile you knew would be there. You were supposed to win dammit. You’d spotted him earlier in the week, knew exactly when he’d be at that bench. You told all the students nearby to tell him 1, that it was for some psychology project. 

You should have known Dean could smell a con, he was too fucking good at it not to. When he’d grabbed your hand and dragged you away from the quad, pulled you over to the library, you knew you were leaving things up to fate. 

Apparently fate was a bitch. You walked in front of Dean out of the library, him right on your heels, over to a secluded side of the building. You finally turned to look up at him and saw that smile there.

“Shouldn’t have tried to trick me, Y/N,” he said, shaking his head. He leaned down to whisper in your ear. “I think you’re going to have to be punished for that,” he said, his words rough. He pulled away and you gazed up at him. He stared you down like you belonged to him and only him. “Give me your phone,” he said, holding out his hand.

He reached into his pocket and handed you his. You put in your number and address, putting in your name at first but stopping when he caught your wrist.

“I think you should put in something more appropriate, sweetheart,” he said and you quickly changed it to his nickname for you. When he handed you back your phone, you saw you now had a ‘Frat Boy’ entry. You found yourself looking up at him expectantly, waiting for guidance from him. 

“It’s only wednesday,” he said, shoving the phone back in his pocket. “I’ll give you a few more days of freedom,” he said, crossing his arms. “Friday night, the clock starts ticking. Rest up, Y/N,” he said, unfolding them and patting you on the head condescendingly as he began to walk away. “You’re gonna need it,” he said, walking backwards with a devilish smile.

You were definitely fucked.

 

It was almost ten when you heard your phone ring. You gulped. You’d been waiting for him to call for hours and were quietly relieved you wouldn’t have to anymore.

“Are you home?” he asked when you answered.

“Yeah, I’m here,” you said. Dean paused before speaking again.

“You got any roommates I should know about?” he said. You smiled. The guy might have been a cocky bastard but at least he was looking out for your modesty.

“No, I live alone,” you said, feeling your heartbeat start to quicken. 

“Good since we’ll be spending quite a bit of time together. I’ll be there in fifteen minutes,” he said, ending the call before you could say anything else.

Fifteen minutes later right on cue you heard a knock at your door and a spark shoot through you. You clicked off the TV and walked over to the door, opening it to find Dean standing outside. He gave you a smile as he walked inside.

“Nice place,” he said, looking around. He kicked his boots off and left them near your pile of shoes at the front. You laughed. “What?” he asked.

“Where on earth did I find you?” you said, rubbing a hand against your head. “A frat boy that’ll fuck me into the mattress but takes his shoes off without me asking? You’re one of a kind Dean.”

“Not everything I do is dirty,” he said, walking towards you. “Wouldn’t want to get your floor all messed up before I fuck you on it,” he said walking around your apartment. Your pussy quivered at the promise and you had to squeeze your legs to calm down, watching Dean smile as he caught you doing so.

“What’s your poison?” you said, walking backwards toward your kitchen to grab the two of you drinks. Dean roved his eyes over you dominantly.

“You,” he said, something dark in his voice. You felt a small shudder run through you to your core. “Whiskey if you got it sweetheart,” he said, following you into your kitchen. You opened up your cupboard where you stored your hard liquor, the whiskey on the top shelf. You had to stand on you tip toes to reach if when you felt Dean press up against your backside, pining you between him and the counter.

“Let me get that for you,” he said, reaching above you and grabbing the bottle. When he pulled it down, he kept up against you tight, pouring a glass for the both of you as he looked down over you. 

He put the bottle down and picked up the glass, taking a sip before lowering it down in front of you, offering you some. You let him tip the glass back so the liquid poured slowly into your mouth, your hands still by your sides. Dean removed it from you lips as you swallowed, downing the rest of it and putting it back down.

“Thanks for the drink,” he said, placing both of his large hands on your hips, holding you tight. You could tell that he was semi-hard when he’d first trapped you, now he was fully erected and you could only imagine what he had in store for you. “I think you should have a chaser with that…” he said, spinning you around and pushing you to your knees in one swift motion. 

Dean unbuckled his belt tantalizingly slow, your own pussy wetting at the show he was giving you. He finally undid it along with his zipper, dropping his jeans and boxers to the floor, revealing him in all his glory. His tip wasn’t as red this time, he hadn’t been worked up for as long, but precum still leaked from the slit. You smiled, proud you could turn him on that much in such a short period of time.

“Now when I say suck this time…” he said leaning over to stare you in the face, “That doesn’t mean soft little kisses from those pretty little lips up and down my cock. It doesn’t mean you pop off to ask if I’m ready, understand? And I don’t want to see a drop of my cum on that pretty face when I’m done,” he said, authority in his voice. You nodded your head in response. He used one of his hands to hook under your jaw and lift your chin up.

“When I say suck, what do you do?” he said hungrily. God you were turned on by him.

“Suck,” you said obediently. Dean brought his lips to yours and gave a harsh and quick kiss, all the while holding your chin.

“Good little girl,” he said, dropping your face and petting the top of your head. You smiled as he did so and realized your mistake when you caught his face. “You like that don’t you? Like it when I praise you for following the rules?” he said, patting you once more.

“Fuck,” you uttered as you felt yourself getting more and more turned on. You hoped he’d cum fast so that he would turn his attention towards you. He chuckled darkly as he fisted his hand in your hair.

“Sweetheart?” he said.

“Yes?”

“Suck,” he said. You wrapped your lips around his swollen tip, licking the precum off and swallowing before continuing to move down his shaft. His tip hit the back of your throat but you didn’t have the urge to gag this time. Dean’s hand guided you until you lips found his base and you swallowed again, the muscles in your throat constricting around Dean’s cock.

“Oh, Y/N. You’re so fucking good at that,” he said, his hand in your hair pulling you back until only his tip was in your mouth. “Love those lips wrapped around my thick cock.”

Dean’s hand moved you forward again and you decided to let him fuck your face at whatever pace he wanted, let him merely guide you as you focused on licking and sucking, swallowing when his length was deep in your throat. Dean’s moans and grunts filled the room as he set a brutal pace, throbbing and twitching all along his shaft.

“F-f-fuck,” Dean stuttered out and you moaned around him, pulling a deep groan from him. You knew he was close as he pumped your lips over his length harder and faster. You pressed your tongue against his length hard and felt him shoot himself in you.

“Y/N! Fuck!” he cried out as you greedily swallowed his cum as his cock continued to convulse within you, your mouth continuing to work him through his orgasm. This time when he pulled out, not a drop came with it.

“You didn’t get any of my cum on your chin this time. See? You are learning to listen to me, little girl,” he said, taking a step back and resting against the counter. “I’ll have you trained in no time,” he said, taking a step forward to pull his pants and boxers back on.

“What are you-” you asked before he cut you off.

“You can get up from the floor now if you want,” he said, tightening his belt and walking out of the kitchen. 

“Where are you going?” you asked, your pussy aching to be touched. Dean smiled.

“Home. Don’t you remember, sweetheart? You’re being punished for trying to trick me,” he said, walking towards the front door. You let out a loud whine.

“Dean, come on. I’ll do whatever you want,” you said, need in your voice. Dean chuckled.

“Sweetheart I’ve got all month to do whatever I want. Tonight all i want is a blow job and to torture you,” he said with a wink as he bent down to tie his boots. You groaned.

“You better not pull this crap all month,” you said as you leaned over him. Dean finished tying his other boot and stood up, towering over you.

“I’ll pull whatever crap I want to pull, little girl,” he said, walking towards you until your back hit a wall. “That was the deal. If I were you, I’d be a little nicer to me if you want me to let you cum.” 

“Sorry,” you said through gritted teeth. Dean’s eyes looked possessive again.

“I guess my good little girl isn’t so good for me, huh?” he said. 

“Sorry,” you said again, failing at trying to sound genuine. Dean placed his arms on either side of you, caging you in. He stared in your eyes before licking his lips and pulling them up into an evil grin.

“Your punishment isn’t over, Y/N. You better not fucking cum tonight or tomorrow or until I tell you that you’re allowed to,” he said, dropping his hands away from you. “You do that and maybe I’ll let you cum at the party tomorrow night.”

“Fine,” you said, crossing your arms. You’d just get off after he left. It wasn’t like he would ever know. 

“Don’t fucking disobey me, Y/N,” Dean said powerfully, snapping you from your thoughts. “I know what you’re thinking and you better fucking not. I’m doing this for your own benefit. You’ve got to learn to follow orders,” he said, watching you carefully. 

You stared at him angrily at first but weakened under his gaze until you were sure you looked defeated. The fight went out of you and Dean knew it. He took the step over to where you were and pet the top of your head.

“You’re not going to cum,” he said. You knew it wasn’t a question.

“I’m not going to cum unless you let me,” you said, telling him exactly what he wanted to hear. 

“You’re a quick learner Y/N. Just follow the rules and I just might let you cum tomorrow night,” he said, leaning down and brushing his lips with yours. You leaned up to kiss him but stopped and pulled back. You felt Dean laugh against you.

“I didn’t say you couldn’t kiss me. Fuck do whatever the hell you want, just don’t cum,” he said. You leaned up and kissed him, letting Dean chase the taste of himself. He pulled away quick and opened your door to leave.

“See you tomorrow night I guess,” you said, still horny but knowing you wouldn’t disobey. 

“Don’t worry, you’ll hear from me sooner than that,” he said with a wink and walked out the door. You shut it closed behind him and slid down against it.

 

Around 4 in the afternoon the next day you got a text from him, “ _Midnight, my room_.” You tried to keep yourself distracted but could only think of what would happen. Was he going to deny you again? Fuck you? You really wished you had won the bet.

You didn’t get to the frat party until close to midnight. You weren’t a fan of going solo but felt comfortable enough knowing Dean was somewhere in the house. It was quieter tonight, the party seeming to have fizzled out. Now it seemed like only actual friends remained. You chugged a beer on the back patio and tossed it in a bin as you walked back inside. No one stopped you as you headed up the stairs to the second floor. 

Once you got up there you hesitated. About five of Dean’s frat brothers were standing in the hall talking. You recognized the really tall one who walked over to you.

“Don’t tell me Dean’s got a girlfriend. I’m sure you’re too good for him,” he said with a friendly smile. “He’s up in his room,” he said, pointing up the next flight of stairs. You thanked him and knew they would immediately start talking about you, urging you to get out of earshot as soon as possible.

Up on the third floor it was quiet. Walking past the rooms, you found that most of them didn’t have occupants, no bedding, no clothes. It was a ghost town. All except for the one at the end of the hall.

You knocked on the half open door and pushed it aside to find Dean laying on his bed reading a book. His eyes lit up and then darkened when he saw you enter and lock the door behind you.

“You look very pretty in that dress,” he said as he stared at the black garment you wore. You kicked off your heels and placed them by the door, giving him a view of your ass. “Is someone trying to impress me?” he said, shutting the book and tossing it aside. He walked over to where you stood up and brushed a stray hair out of your face.

“Easier than jeans,” you said hopeful. Dean chuckled as he walked around you, taking you in. His fingers gave ghost touches up and down your arms, across the small of your back.

“Did you listen to me?” he said, coming to a stop in front of you. You rolled your eyes and crossed your arms. “I’ll take that as a yes,” he said. He moved the fabric covering your shoulders down, letting it slip down until you were standing there in nothing. Dean let out an involuntary moan as you bit your lip. You hadn’t worn anything underneath.

“Thought you’d like that,” you said. Dean took your hand and led you over to the bed, plopping down when your knees hit.

“Such a fuckin’ tease,” he said, using one hand to push your chest so that you lay against the bed. “Don’t touch,” he warned as you moved your hands towards him. His hands roamed over your breasts, squeezing and playing with them as you kept your hands clenched in the sheets.

“Who’s the fuckin’ tease?” you said as Dean rolled your nipple between his thumb and forefinger, the pleasure starting to build in you. Dean eyed you devilishly before brining his mouth down to the other one, licking and sucking at it, your back arching as he grazed the sensitive peak with his teeth. 

“You want to touch me?” he asked, as he pulled away, kissing his way down your body. You bucked your hips in anticipation. Dean pressed a hand down, keeping you from doing so again. “You think I’ll fuck you? Think I’ll let you fucking cum if you touch me?” 

“Please Dean,” you begged as his lips stopped on your mound. He was so close to where you wanted him. You went to squeeze your legs together but a rough hand prevented you from doing so.

“You’re already dripping little girl. That pussy is so wet, I bet you taste delicious,” he said, his mouth just inches from your soaked folds. You whined and it must have sounded pathetic because the next thing you knew, Dean leaned up and gave you a soft kiss, something you’d never gotten from him before. He wasn’t as demanding as normal and when he broke away, he pet the top of your head.

“Shh, you’ve been very good. No more teasing,” he said, lowering himself once more. This time he didn’t hesitate as he took your clit in his mouth.

“Oh shit,” you squealed out, Dean’s tongue ravishing the bundle of nerves. You squirmed as he used one hand to keep your hips flush against the bed, the sudden intensity and the denial of your orgasm last night building you up fast. “Dean…” you moaned and felt him smile against you. 

Your hands fisted the sheets so hard you barely felt it when Dean’s free hand tapped the top of one. He looked up at you, silently telling you that you could touch. Instantly your hands shot into his hair, tugging on it and pulling a moan from Dean as he worked you over.

“G-gonna…” you got out as you tried to hold back your orgasm. Dean nodded against you, giving you permission to cum. That was all you needed as you cried out, your breaking point hitting you.

“Dean!” you yelled, not caring who heard. Dean’s assault on your clit continued as you came down, the bud now overly sensitive. Dean pulled away to catch his breath as he gave you a wink. You leaned your head up to smile at him when he went down again, this time leaving a long stripe on your folds. 

You moaned excitedly as you felt his tongue tease your folds, slowly dipping in. Your hands fisted in his hair tightly at the feelings he was creating within you. You saw him wince just slightly and you let go, give him a soothing pat on the top of his head as his tongue delved further into you. 

As soon as he moved his tongue, swirled it, you felt a hidden orgasm surface, the thing already so close to coming crashing down you knew you’d cum faster than he wanted. 

You felt Dean mumbled against you as you leaned up to see his eyes looking at yours as he continued to move within you. You fluttered your eyes, your pupils blown, licking your lips. Watching him eat you out was divine. 

He mumbled again and you saw that he didn’t want you to hold back anymore. You did as he wanted and felt your walls clamp down around his still thrashing tongue, the movement prolonging your orgasm.

“Fuck!” you screamed as you felt yourself gush into his mouth, Dean’s tongue lapping up everything you had to give. Your chest heaved as Dean pulled away, climbing on the bed and hovering over you.

“God that little cunt tastes so fuckin’ good,” he said, brining his lips to yours so that you could taste yourself. You liked it, but found yourself missing the taste of him. Dean pulled away and plopped down besides you, trying to catch his breath. You stared at him and saw his face still glistened with some of your juices. You leaned over and licked some of it off, savoring it.

“Dirty fucking girl,” he said pleased as you continued to clean yourself from him.

“Dirty fucking  _little_   _girl_  to you,” you said when the last of it was gone. Dean smiled as he pulled you on top of him. You felt his hard member behind you as you realized Dean was no longer wearing any clothes.

“When did you do that?” you asked, raking your hands across his chest, feeling the muscles underneath the skin. 

“After your orgasm sweetheart, when do ya think?” he said, his hands resting on your hips. He was still breathing a little heavy, it’d been so long since he could get a full breath.

“You stay right there,” you said as you lifted yourself and scooted back, lining yourself up with his cock. Dean’s hands helped lower you onto his member, a groan erupting from him, a welp from you as you ground down on him fast.

“Fuck,” he said, as you raised yourself almost all the way off and pounded down again. You moaned at the feeling and did it again. You set a rough pace, pulling beautiful grunts and groans from Dean’s lips as you rode him over and over and over.

“Such a tight little cunt. Fill up that cunt so fucking good,” he said as you slammed down, a pleasurable laugh erupting from him. “Keep that up and you’ll kill me,” he said and you smiled wickedly. You slammed down on him hard, pulling the same sound from him. His hands went to his hair and you moaned. He was putty in your hands now.

You kept up the rough pace of slamming onto him, each thrust hitting your G-spot again and again. You were close but held off for him, you loved the sounds he was making too much to cum just yet.

“Y/N, I’m close-” he said, voice needy but just as authoritative as ever. You doubled your efforts, both of you chasing your ends as he throbbed inside you.

“Go ahead and cum. Fill up my pussy with your cum,” you said and slammed down harder than ever before. A strangled cry came from both you and Dean at the same time, your orgasm’s occuring simultaneously. 

Dean’s cum splashed within you as your pussy constricted him like a snake, holding on to him like a vice. You fell onto his chest as you both rode out your highs. Dean’s face was pure bliss. When he stilled within you, you pulled off of him, brining your face down to his still hard cock. You wrapped your lips around his length and bobbed your head up and down a few times, licking him clean as Dean’s hands found themselves in your hair.

“Fucking christ woman,” he said as you climbed back up to him, resting your head on his rising and falling chest. He wrapped an arm around you and pulled you in close, his hot breath on the top of your head.

“Thought it was little girl,” you joked, Dean’s hand rubbing up and down your arm. 

“Do you want to get punished again  _little girl_?” he said, a threat in his voice. You titled your head so you could look up at him, a pleading no in your eyes. “Exactly,” he said, the two of you laying there in contentment. 

After a while of Dean cuddling you, you felt a hand under your chin. You looked up and wondered if you were about to start all over again, but his face said something different.

“You have plans tomorrow morning?” he asked darkly. 

“No,” you answered. Dean smiled and let go of you.

“Okay. You can either go through the effort of getting dressed, going home, etc. Or you can stay here tonight,” he said. “Either way I expect you to be here when I wake up in the morning. I’ve got some things planned for you,” he said, his fingers brushing your cheek. 

You leaned your head down on his chest and shut your eyes. He was much more comfortable than your bed anyways. “Goodnight, frat boy,” you said. You felt Dean shift to pull the covers over the two of you.

“Goodnight sweetheart,” he said, kissing the top of your head. “See you in the morning,” he said, a promise in his words. 


	3. Chapter 3

**Summary for the Chapter:**

> Dean and reader get a surprise…

“Dean!” you heard a voice say as it barged into the room. You flung open your eyes as both you and Dean shot up in bed, pulling the covers over yourself. It was the tall frat boy. He was dressed in a nice looking suit. “Get up!” he said, moving to Dean’s closet and pulling out a similar suit.

“Sammy, dude!” said Dean, nodding towards you. You held up a hand and gave an awkward wave as Sam noticed your heels by the door, dress on the ground.

“Sorry,” he said to you before turning his attention towards Dean again. “Come on you gotta get dressed!” he said, tossing the clothes at Dean. Dean rolled his eyes.

“Why do I-”

“Mom, dad, brunch today? They’re downstairs for christ’s sake,” he said. “I’ll hold them off as long as I can but you know mom will be up here in no time,” he said, leaving and pulling the door shut behind him. You looked at Dean who looked just as bewildered as you.

“Well this wasn’t what I had planned this morning,” he said, rolling out of the bed and digging through his drawers to find a clean pair of underwear. You got out of the bed and dashed over to your dress, pulling it on as Dean pulled up his dress pants. “Was hoping to wake you up a more fun way,” he said with a wink.

“Next time,” you said, running your fingers through your hair. You helped Dean button his shirt, when you heard a knock on the door. Dean’s hands were on you in an instant and pointed you towards his bathroom. You’d just made it in and shut the door when you heard footsteps enter the room. You couldn’t hear anything but soon the door was opening.

“I’ll just be a second, Dean- Oh! I’m so sorry dear! Didn’t know it was occupied,” a nice, middle aged blonde woman said before pulling the door shut. You decided to suck it up and walk out, ready to face whatever comments came your way. When you got out there though, you found none.

“I wish I still looked that good,” she said to you. “See Dean? Your girlfriend is wearing a beautiful dress, you can wear a tie,” she said, walking past you and patting you on the shoulder. “I’ll be right out and then we can head out, okay kids?” she said as she entered the bathroom behind you. You shrugged your shoulders as you ran over to Dean. 

“She thinks you’re my girlfriend and that I’m still…I don’t know…not the cocky asshole I am. Please, Y/N, can you-”

“Your secret’s safe with me,” you whispered. “What about…I guess he’s your real brother too?” you asked. Dean nodded his head, telling you Sam was good.

“Alright, let’s go! Reservations at 11. I don’t think they’ll mind one more,” said Dean’s mother as she left the bathroom, waving the two of you out of the room.

 

“So, how did you two meet?” said John, Dean’s father. You saw Sam smirk and Dean kick him under the table. 

“Party,” said Dean truthfully. “Some jerk was trying to get her to sleep with him so I pretended to be her boyfriend to get him to leave her alone,” said Dean, watching you carefully.

“Yeah Dean really looked out for me, never tried to make a move on me or anything,” you said, putting on your best acting. The both of you could tell Sam was fighting back laughter. “I’m lucky to have him,” you said, putting your hand on his thigh, rubbing it slowly out of view of the others.

“No, I’m the lucky one sweetheart,” he said, his hand finding your thigh now, giving you the same treatment. Only difference was, you still weren’t wearing any underwear and Dean knew it.

“Keep this one around son. I think she’ll be good for you,” said John as he took a sip of his drink. You felt Dean’s hand slip down further and push your dress up only slightly so that he could move his hand underneath. Fucking frat boy was going to touch you right there at the same goddamn table his entire family was sitting at, just a foot away.

“Oh, I don’t plan on giving her up,” Dean answered as you felt his fingers brush against your clit. You inhaled sharply and covered it up with a cough as he worked slow circles around your bud, driving you nuts. If only his mother, Mary, knew her son was more of a devil than saint. 

“So what do you study, sweetheart?” asked Dean’s mother. You weren’t used to anyone calling you that besides Dean. 

“Um…” you said as Dean increased the pressure on your clit, pressure building up in you. God you’d kill him once his parents were gone. “History,” you got out without stuttering. You couldn’t even remember what the hell kind you’d spent the past few years learning about you were so focused on trying to control yourself. “I plan on going to grad school,” you said, coughing again to cover up a rising moan.

“You okay, Y/N? Coughing quite a bit,” said Dean with an innocent smile. You knew a far darker one lay hidden underneath. You smiled back and took a sip of your water. You caught Sam’s expression change, for only a moment, as he realized what was going on.

“I’m going to the bathroom,” Sam said suddenly, standing from the table quickly. You saw as John and Mary both stood.

“Good idea. That mimosa is starting to hit me,” said John as Mary asked if you two would watch her purse. When the three of them were gone, you gave Dean a death stare.

“What the fuck are you doing?” you said quietly, Dean’s finger picking up the speed now that you didn’t have such an observant audience. He smirked and licked his lips.

“Whatever I want, whenever I want. Sound familiar?” he said as he pushed hard against your clit and you had to bite your lip to keep quiet. You would have retorted but his fingers were doing such wonderful things to you, you didn’t dare open your mouth. “If I were you, I’d cum before they got back,” he whispered in your ear as you felt yourself break. Your mouth opened involuntarily but Dean captured your lips with his before you could make a sound, swallow the moan that came with your orgasm. 

You felt him move his hand from you at the same time as his family came back into view. He picked up a napkin and wiped his finger clean. You smirked. At least he wouldn’t get to taste you and you knew he loved to.

“You two love birds ready to head out?” said Mary as she picked up her purse. You and Dean shared a look as you saw his parents chuckle. “We saw you two,” she said pointing at the pair of you. “Embarrassed to kiss your girlfriend in front of us Dean?” she said. Dean shook his head.

“Something like that,” he said looking at you, just a hint of that devilish smile breaking through. 

 

Somehow you ended up spending the day with Dean, and his brother Sam who was his frat brother too you guessed, and their parents. They were really nice people and you found that Sam was a history major too, just a year younger. You made sure to keep your distance from Dean the rest of the day and when his parents finally left, you could tell he was annoyed with you.

“I thought we had a deal,” he said as you sat on the couch at their frat house, the stench of beer coming from it.

“Dean,” said Sam, walking back into the room and handing each of you a beer. “I mean I know you two have some friends with benefits thing going on-”

“He’s not my friend,” you said defiantly. How you had been so submissive to him before you had no idea. All you knew is it wouldn’t be happening again. Dean glared at you and crossed his arms.

“Whatever this is,” said Sam, waving at the air between you two. “Don’t be a complete dick to her. You were torturing her,” said Sam to his brother. Why couldn’t you have hooked up with  _that_ frat boy…

You looked at Dean who didn’t seem to know what to say. You handed the undrunk beer back to Sam with a smile.

“Thanks, Sam but I think I’m going home,” you said as you stood. “Alone,” you said as you walked past Dean. 

Once you got there, you had a nice long shower, and threw on some sweats and a baggy t shirt, your hair up in a messy bun. You ordered a pizza, opened a bottle of wine and turned on a movie, ready for the day to be over and forget about Dean. You heard your doorbell ring and hopped up quickly, ready to dive into your food. You opened the door to grab it when you instead found a familiar looking face holding your box.

“Hey,” said Dean a little sheepish. You ripped the pizza from his hands and tried to slam the door but Dean caught it before it could do so. “Can we talk?” he asked. You rolled your eyes but waved him in anyways. You heard him shut the door and take off his shoes behind you as you placed the pizza on your kitchen counter. You opened it and pulled out a slice, taking a bite and savoring it before seeing Dean still standing near the door. You walked over to your living room and sat back on your couch.

“You wanna talk, talk,” you said, taking another bite. Dean walked around to the other end of the couch and took a seat. He fumbled with his hands as he looked at you nervously.

“I went too far this morning,” he said, a laugh erupting from you as soon as he had the words out. “I’m sorry,” he said. For a moment you thought it was genuine. 

“Whatever, frat boy. Should have expected that kind of behavior from you,” you said, setting the pizza down and crossing your arms. 

“I mean it, Y/N. I really am sorry,” he said. You looked at his eyes and scolded yourself. He fucking meant it and now you didn’t know what to do.

“Don’t ever fucking do that again. ‘Whenever I want’ doesn’t mean in front of other people, especially if you don’t fucking ask my permission first,” you said. Dean looked small, not the cocky frat boy you were used to.

“Do you want to stop?” he asked. You paused, letting him squirm for a few moments.

“Fuck no,” you said with a smile. “But we’re adding a rule,” you said moving to stand in front of him.

“Don’t do that again,” he said, avoiding your gaze. You reached out your hand and took his chin in it, forcing him to look at you. Fuck, now you knew why he loved doing that to you. 

“If it’s something new for us, or something risky, you ask me, understand?” you said. He nodded obediently and you smiled. You dropped your hand and watched him as he breathed deeply, his breath catching in his throat. “Are you turned on frat boy?” you asked playfully. 

“No,” said Dean, a waver in his voice. You raised your eyebrows and smirked.

“Frat boy, my cocky frat boy, so controlling, so dominant and he’s getting fucking turned on by being in trouble, isn’t he? He wants to be punished?” you said, licking your lips. You looked down and saw the bulge in his pants. You placed your hands against the couch on either side of his head and leaned down. “Well ya gonna answer me frat boy?”

“Just tonight you’re in charge,” said Dean, his voice still submissive. You smiled as you leaned down to whisper in his ear.

“We’ll see frat boy,” you said leaning back. You pulled your shirt off with ease and stepped out of your pants, kicking them to the side. You grabbed him by the shirt collar and lifted it upwards, helping him pull the garment off of him. Your hands made quick work of his belt and you pulled his jeans down easily, leaving the two of you in just your underwear. You ripped his boxers off, leaving him sitting on your couch naked, hard as a rock.

You reached behind yourself to unclasp your bra before dropping your underwear. You placed your hands on either side of his head again as you pulled your knees up, straddling his lap. Rolling your hips forward, you lined yourself up with his cock before lowering yourself down slowly.

Dean moaned as he felt you grip him tightly, your pussy taking him deeply. You enjoyed the feeling of him filling you as you moved your hands to his body, roaming over his chest and abdomen, running them up his arms. He hardly ever let you touch him you didn’t realize how strong he truly was.

You opened your eyes, not realizing you’d shut them in the first place. Dean was watching you patiently and you caught something unfamiliar in his eyes before disappearing. 

“It’s okay, you can touch me. I’m not as mean as you,” you said as you ever so slowly moved your hips. You felt Dean’s hands run across your body gently, his fingers running soft circles over the bruises he’d left on your hips the night before.

“You’re so beautiful,” he said as you rested your head against his shoulder, slowly raising and lowering yourself on him over and over again. “Why the fuck don’t you have a real boyfriend?” he asked. You turned your head so you could face him.

“Nice guys don’t fuck me like you do,” you said, increasing your speed just slightly. Dean laughed as his lips peppered your shoulder with kisses.

“Can a guy that fucks you like me be a nice guy?” he said. You picked up your speed again. You knew what he was asking.

“Don’t know yet. I barely know anything about said hypothetical person,” you said. Dean’s lips found your neck, leaving gentle kisses there.

“Guy’s probably an ass,” he said, kissing your jawline. You smiled at the feeling as your hips worked in perfect symmetry with Dean’s.

“Probably. He’s pretty good at apologizing though,” you said, both of you rolling your hips hard, your orgasm’s hitting you at the same time. You moaned as you felt Dean cum inside you, your walls clenching him and helping him ride his high. Dean’s lips were on yours as you rested against his shoulder, his kiss gentle. He helped pull you off of him and lay besides him.

“I liked that, being…slow,” he said, turning to look at you. You sat up and walked over to where his clothes were, tossing them to him.

“Every once in a while doesn’t hurt,” you said. “But tomorrow night you better fuck me hard and be calling me a dirty little girl, got it?” you said, throwing your shirt back on. Dean quickly put his clothes on and shook his head. He smiled as he put his boots back on and a hand on the door.

“Anything for my sweetheart,” he said with a wink.


	4. Chapter 4

**Summary for the Chapter:**

> Dean and reader take a few days off for midterms before continuing their game…

“Night Stacy!” you said as you skipped down the steps of her house after your study session. Dean had texted you earlier saying he had to study for his midterm in the middle of the week and you were relieved you wouldn’t have to tell him you needed to study for your test as well.

After last night, Dean was a little different towards you, even if you’d only texted since then. You could sense that he didn’t feel like he had to keep up the cocky charade around you all the time now. Sure, a part of him probably was like that, but you guessed it was much smaller than he let on. 

The cool October air was a little chilly as you tucked your hands into your hoodie. Your backpack was heavy, you hadn’t planned on staying that late and you were tired as a result. You let yourself enjoy the night air on your long walk back to your apartment. 

A twig breaking behind alerted you that you weren’t alone. You tossed a look over your shoulder and saw two guys a distance back, leaning against someone’s front fence. They hadn’t been there when you passed but figured they lived there and just went outside to get some fresh air. Still, your hand tightened around your phone in your pocket.

You walked on when you heard another snap. You looked back more slyly this time so they wouldn’t see you. Now there were three of them. And they were closer.

“Shit,” you muttered to yourself as you pulled out your phone. You put in a number without thinking twice and desperately hoped he would pick up.

“Hey, Y/N,” said a tired voice. It was almost midnight, you hoped he hadn’t been in bed. “What’s-”

“I’m on Stanson,” you said, trying not to let on how scared you were, “Coming from the north side of campus, and t-there are these guys following me. It’s p-probably nothing and I’m-”

“Don’t get off the phone. I’ll be there in two minutes,” he said, worry in his voice. “You just keep talking to me,” you heard him say as you heard his feet pound down one flight of stairs and then another. “Y/N, talk to me,” he said authoritatively, a door slamming shut in the background.

“I’m still here. Um…” you said, unsure of how to remember how to speak at that moment. You looked behind you and saw the three men walking behind you, too close for your comfort. “Please hurry,” you said, walking faster.

“I’m here sweetheart, I’m coming for you,” he said between heavy breaths and for a moment you thought how lucky you were to have a boyfriend like that. But Dean wasn’t that to you. He was just…Dean. “Y/N, please keep talking, you’re scaring the shit out of me,” he said, jarring you back to reality.

“S-So how’d s-studying go?” you asked, a wince in your voice. “Shit,” you said as you heard the footsteps behind you get louder.

“I’m almost there, I’m almost-” you heard before your phone started beeping. You looked it and saw the call had been dropped.

“Oh fuck,” you said, picking up your pace to a jog now. You heard the footsteps behind you increase and you could only imagine every horrible thing that was about to happen.

“Y/N!” you heard a loud and angry voice call out in front of you as you saw Dean round the corner in a tee and pair of sweatpants. You ran at him at a full sprint until you nearly toppled him over, letting him wrap his arms around you for only a moment before they pushed you behind him. 

You heard the three pairs of feet behind you stop as you peered around Dean to look at them. One of Dean’s arms wrapped behind himself, holding you close to him. Obviously the three were determining if they could take on Dean or not.

“Take one more fucking step towards her and it’ll be the last thing you ever do,” said Dean, so much anger and rage in his voice it almost frightened you. You watched from behind Dean, as your hands clung into the back of his shirt as the three turned and ran the other way. If you had to guess, Dean probably looked fucking terrifying at that moment. They were long gone by the time Dean had calmed down enough to remove his arm from you.

“Dean?” you asked, taking his still shaking hand in your smaller one. He looked down at you and you saw his anger melt away. His hand brushed your face.

“Are you okay?” he asked and you nodded your head. “Come on,” he said. “I’ll take you home.”

“C-can I stay with you?” you asked as Dean took a step forward. Only then did you notice he was barefoot. His feet were probably ruined from running over to you so quickly.

“Of course,” he said, wrapping an arm around your shoulder. Even if you were both shook up, the five minute walk back to the frat house was one of the most enjoyable of your life. You’d never felt safer. When you opened the front door, you found Sam and what looked like all of their frat brothers sitting in the front room.

“You guys okay?” asked Sam, who you gave a small smile to before looking away. 

“Woke up the whole house with your yelling Dean, figured something was wrong,” said a shorter, black haired one. Dean gave your shoulder a light squeeze.

“Somebody trying to mess with, Y/N is all. I took care of it,” said Dean, tapping you on the shoulder. “Let me get that, you’re tired,” he said, pointing to your backpack. You shrugged out of the straps and handed it over, knowing Dean wouldn’t take no for an answer right now.

“Nobody messes with our house. Dean’s ever not around, just let us know, Y/N and we’ll go kick their ass,” said a frat member you’d never seen before. You nodded sheepishly as the group of young men reiterated his statement in more than a few ways.

“Do you guys have a first aid kit?” you asked to the group and you saw Sam bolt up and run into the kitchen.

“You hurt?” asked Sam as he walked back in and handed it to you. You looked down at Dean’s feet that he was trying not to put too much weight on, an impossible task. “You didn’t put on shoes?” he asked his older brother.

“I wasn’t going to risk wasting any time,” said Dean a little defensive. You patted him on the shoulder as he slung your backpack onto his back.

“Excitement’s over for the night. It’s midterms this week so everybody get to bed,” you said and to your amazement, every single one of them listened to you. 

Dean made sure you were close as you followed him to his room, checking over his shoulder every so often to make sure you were there.

“Afraid I’m gonna run off?” you asked as Dean slid your pack off and placed it near his in his room when it was just the two of you.

“Taken’s more like it,” he said as he sat on his bed, his words making you shudder. “I’m sorry, I didn’t mean to scare you,” he said. You smiled as you urged him to scoot back on the bed so you could look at his feet.

“You don’t scare me,” you said as you thankfully found only a few small cuts on the bottom of his soles. 

“One night of slow sex and saving you the next with nobody getting any? You must be wondering where the hell your cocky frat boy went,” he said as you dabbed some rubbing alcohol over his wounds.

“My cocky frat boy…” you said as you found a roll of bandages and started wrapping up his foot. “Is not just dirty talk and dominating in bed. Maybe he should stop acting like that all the time and realize he’s the one I call to keep me safe, the one I trust to do those kinds of things to me in bed?”

“What about that first night when we played pool? How could you-”

“I don’t know Dean. I just knew you wouldn’t hurt me was all. No idea why but turns out I was right,” you said as you wrapped his other foot. Dean said nothing more as he watched you work until you patted him on the ankles. “All done,” you said, tossing the medical kit to the side.

“Here,” said Dean, kicking his feet over the bed and walking to his dresser. He pulled out a t-shirt and tossed it to you. “To sleep in,” he said as you kicked off your shoes. You dropped your jeans next, your socks, your shirt too. You took off your bra too and to your surprise, saw Dean had turned his back to you, giving you privacy. The shirt was soft and smelled like him. You felt better having it on.

“Thanks,” you said, climbing on top of the bed and between the sheets. Dean turned around and got in besides you, turning his bedside lamp off in the process. You felt Dean throw an arm over you protectively before tensing and reaching to pull it away. You grabbed his hand, letting him know it was okay. He relaxed again and this time, pulled you in close.

“Hey, Y/N?” asked Dean sleepily. You turned around so you could face him, Dean’s arm still over you. You nodded. “I’m glad you stayed tonight. I don’t want you alone.”

“Me too,” you said and absentmindedly leaned up to kiss him. You felt Dean kiss you back before both of you broke away. “Goodnight Dean,” you said, turning away from him once more.

“Goodnight, Y/N,” said Dean as you felt him nuzzle his head against the back of yours. You fell asleep so easily that night you forget you were ever scared in the first place.

That was until you woke up with a startle. You’d had a dream, well a nightmare, about the night before, about Dean not getting to you in time. You let out a heavy sigh when you realized you weren’t at home, Dean sleeping right besides you. Turning your head to look at him, you found a pair of nervous green eyes.

“Was I yelling?” you asked, afraid you’d woken him. He shook his head no as he used his arm that was around your waist to turn you towards him.

“Couldn’t sleep,” he said, using his other arm to pat the top of your head. You closed your eyes and smiled. “Figured you’d like that,” he said as he turned the motion into smooth strokes, his fingers stopping to play with your hair. You didn’t say anything as you just watched him, letting your nerves calm, letting him calm his own. You shut your eyes as you grew tired, Dean’s hand eventually stopping as his breathing slowed, sleep overtaking him. The last thing you remembered was how peaceful he looked.

 

“Ugh,” you both said as the sound of Dean’s alarm clock blared through the room. Dean let go of you to throw his arm in the direction of his bedside table, smashing it down until the noise came to a stop. 

“Thank god,” he mumbled as he threw his arm back around your waist and pulled you in tight as he curled in a ball, tucking you in with him.

“We’ve got to get up,” you said, wishing you could just lie like that with him the whole day. You heard him mumble something against the back of your neck as he squeezed you tighter and threw his legs around you.

“You can get up,” he said a little louder and you laughed. 

“Are you going to let me go?” you asked, testing your strength against him and finding it useless, which surprised you. You weren’t a weakling but then again, he was strong enough to scare away three grown men with just a look.

“No,” he said, his voice sleepy but a little giggly.

“Then how am I supposed to get up?” you asked, trying to turn your head to look at him. You felt him shrug, moving your body along with his.

“I can’t solve all your problems, Y/N. You’ve got to be a big girl,” he said and you chuckled.

“What if I want to be a  _little girl_?” you asked, accentuating the last two words. You felt Dean’s grip on you relax.

“Little girl’s going to have to wait until tomorrow night. You’ve got a big test today and I’ve got one tomorrow,” he said, letting go of you. “Why did we decide to do this during midterms?”

“Worried about losing out on your days?” you said, sitting up and twisting your back. You caught that look in Dean’s eyes again and twisted the other way. Suddenly you felt Dean’s hands on your hips, finding their way underneath his long shirt you wore.

“Should I be?” he said as he ran light circles over your skin. You felt a jolt run through you, straight to your core but to your whole body this time too.

“Tomorrow night,” you said, turning your head over your shoulder and grinning as you caught sight of his messy bed head.

“Alright,” he said, his face just inches from yours before pulling away and grabbing your hand. “Breakfast and then I’ll walk you to your place so you can change and then I’ll take you to class,” he said, swinging his feet off the bed and jumping onto the ground. “Ow,” he said through gritted teeth as he felt the cuts on his feet.

“My hero,” you said as Dean’s face returned to normal, expecting the slight pain with each step. “You don’t have to walk me everywhere if you don’t want to, it’s daylight…” you trailed off when you caught Dean’s face. He was still shook up. 

“Let me today,” he asked as he put his hand on the door handle, his other one wrapped around yours. You smiled and he relaxed. 

“So what’s for breakfast?” you asked.

“Breakfast? I just wanted to show you off in my shirt,” he said with a wink as he led you down the stairs. 

 

“How’d your test go?” asked Dean as you sat next to him at a table in the student lounge. 

“Easy,” you said, opening the styrofoam container you’d dropped on the table full of your dinner.

“This is gonna suck tomorrow,” said Dean as he sat buried in notes. You gave him a sympathetic smile.

“I’m sure you’ll do great, Dean,” you said.

“So do I,” said a voice behind you. It’s owner walked around to the other side of the table.

“Could you make it a little easier for me and give me the answers ahead of time professor?” asked Dean. 

“You got all the answers right there, and there, and some over there,” he said, pointing at Dean’s study materials. “Hi, Y/N,” said the professor turning his attention towards you.

“Hey, Nick,” you said to the older man. He gave you a friendly smile as Dean watched you carefully.

“I didn’t know you were friends with Y/N,” said Nick to Dean. “I’m sure she’ll lend you her study materials from my class. One of the few to ever get an A in it,” he said as he eyed you.

“Yeah, sounds like a good idea, Nick,” said Dean with a tone. “Why don’t we go do that?” said Dean, packing up his things. Ordinarily you’d gripe that you just sat down, were starving, etc. But you knew that tone. You followed suit as Nick kept an eye on you.

“Don’t study too hard,” said Nick as Dean threw his backpack on. Then he turned to you. “You know I’ve been thinking about getting a teaching assistant, Y/N. I think you’d be great,” he said, staring down at you. You looked over your shoulder to see Dean irritated and waiting for you.

“I’ll think about it,” you said loud enough for Dean to hear. A smile lit up across Nick’s face.

“That’s great! You know where my office is if you decide you’d like to do it,” he said as you turned to walk with Dean.

“Let’s go to your apartment to study,” he said, barely letting you catch up. “Less noise.”

Dean passed out on your couch covered in your old flashcards. You thought about trying to drag him to your bed but threw a blanket on him and called it a night. He insisted on walking you to main campus again before he separated from you for the day. You saw how on edge he was and just hoped he’d feel better when you saw him that night.

 

“Hey! How’d it go?” you asked as you opened your front door to let Dean in. He kicked off his boots and put his backpack down besides them as you shut the door. He walked away from you and straight into your kitchen, opening the cabinet with the hard liquor. “Was it bad?” you asked, as Dean poured himself a glass of whiskey and downed it quickly. “Really bad?” you whispered.

Dean turned to look at you just briefly before putting the glass down and opening up your fridge, taking out some leftover pizza from the night before. He devoured it and poured himself another glass, swallowing that in one long sip. You knew it must have been bad if he was this quiet. He put the bottle back and placed the glass in your sink before grabbing you by the wrist and dragging you into your bedroom.

“Dean!” you squealed as he pushed you softly onto your bed. He looked ready to devour you.

“Test went awesome thanks to your notes. You sleep with Nick?” he asked as you sat up.

“Yeah,” you said without hesitation. Dean looked a bit taken aback at your forwardness. “It was after I was out of his class. I don’t sleep with my professors,” you said as Dean pushed you back gently on the bed, leaning over you so you crawled back, giving him room to crawl right on top of you.

“Do teacher’s assistants sleep with their professors?” he said, staring down at you. His eyes weren’t angry but he wanted you to think you were in trouble.

“He was a one and done. I only said that to get you riled up,” you said as you leaned up, forcing Dean to lean back into a kneeling position. “Looks like it worked,” you said, lifting yourself up to kneel and lean even further over Dean.

“What was he like?” asked Dean as you crawled over him, forcing him to lean back, propped up on his elbows. You smirked and raised an eyebrow.

“Frat boy jealous?” you asked, running your hands over his wrists. He could easily overpower you and you were sure he wanted to, but he’d have to risk flipping you off the bed and you knew he’d never let that happen.

“I’m supposed to-” he said through gritted teeth, staring up at you with helplessness. 

“Punish me for making you jealous? Punish your sweetheart, your little girl?” you said, face hovering over his, hands holding his wrists tightly. 

“As soon as you get off of me, you’re going to regret this,” he said with a cocky smile. 

“How bout I just get you off and we’ll call it even,” you said, lowering your face so that your lips brushed his cheek. He laughed. 

“How the fuck are you going to do that? We’re both still dressed and if you move those hands of yours-” he said before you brought your lips to his, invading his mouth like he had done so often to yours. He fought for control but as you squeezed his wrist he backed off, letting you call the shots.

“Good little boy,” you said as you pulled away panting. Dean nodded his head with a scoff between his deep intakes of air.

“I am not your good little boy,” he said indignant. You smiled as you kissed his stubble covered jaw, the hairs tickling your skin. Your lips sucked on his neck hard, marking him. Dean inhaled sharply and you could feel him growing beneath you in his jeans.

“Good little boy is getting hard for me,” you said, moving your hips back, rolling against his erection. Dean moaned at the feeling and you did it again, pulling an even longer one from him this time. “What are you?” you asked and Dean went silent. You rolled your hips against his now full erection, long and slow, putting pressure on him so he’d feel every inch of it. Dean moaned and dropped his head back. “What are you?” you asked again.

“Your good little boy,” he whined as you rubbed your hips hard against him. Even if you weren’t feeling much with the treatment you were giving him, you could feel your underwear was soaked with how much you were turned on.

“You want to cum? Be a good little boy and cum?” you said as you leaned farther over him, pressing against his wrists harder. Dean whimpered but you knew it wasn’t from pain. With the new angle, you could keep rubbing him, gave him more of an illusion that he had to lie back and take it. You could tell he was giving into that as his hands balled into fists and he struggled only so against you, not enough to break away, but enough so he could feel you hold him down.

“Y/N, please,” Dean said as beads of sweat pooled on his head. You could feel your own thighs tiring but fuck you were determined to make him cum without either one of you shredding a piece of clothing. “Gonna-”

“Not until I give you permission,” you said as Dean became a withering mess beneath you. “You don’t cum unless I let you,” you said.

“I’ll be good. I promise. I’ll be your good little boy,” he said as he desperately held off for you. Not long ago on the other side of your bedroom wall had he denied you the experience of cumming. Lucky for him, you had other plans.

“What are you?” you asked again as Dean’s hips tried to buck up unsuccessfully, his legs bent back underneath him preventing him from thrusting towards you.

“Your good little boy,” he said, a moan escaping from his lips that told you he was right on that edge. 

“Go ahead. Cum for me little boy. Cum for me now,” you said as you rolled hard against him.

“Y/N!” Dean shouted as he dropped his head back, a dark spot growing on his pants. You gently rocked your hips against him to help him ride out his high. His chest puffed out beneath you as he let out a large breath and fell back, his head hanging off the bed. You smiled as you released his arms and climbed off of him.

“And neither of us even got naked,” you said as you stood and walked in front of him, giving him a wink. His pupils were still blown, his face in post-coital glow. He smirked as he caught his breath.

“You’re gonna have to show me how to do that to you,” he said, closing his eyes, forgetting he ever wanted to be in control in the first place. You walked out of the room and opened up a small hall closet before returning to him. 

“I’m sure you’ll figure it out,” you said, tossing him a few towels before moving over to where you’d left the clothes you’d borrowed from him on Monday night and tossing them as well. “Clean yourself up while I make us dinner,” you said, grabbing his hand and pulling him up into a sitting position.

“I could have flipped you over if I really wanted to,” he said as you helped him stand. You gave him a skeptical look as you waved for him to follow after. “I know where it is,” he said, walking past you with a grin and to your bathroom right outside your room.

“You didn’t really want to though. You know why?” you said, crossing your arms and cocking your head. Dean raised his eyebrows and dropped his things on the floor, crossing his arms to match yours.

“Why’s that?” he asked with a cocky smirk.

“Because you’re my good little boy,” you said, and you saw Dean shift on his feet. 

“Am not,” he said with no conviction.

“Uh huh,” you said, licking your bottom lip slowly, like he had when you first met. His lips parted just so at the movement, his eyes watching them hungrily. “It’s okay. I won’t tell anyone my cocky frat boy is a good little boy for me,” you said as you turned to walk away. You heard him utter a happy sigh as you left him to make some food for the two of you.

“Don’t fuck this up,” you heard him say to himself as he shut the door behind him.

 

“Such a lovely place,” you said as Dean walked into your kitchen and smiled, his hair still damp. He sat across from you at your small two person table, a plate of pasta and white sauce in front of you both with a bottle of red in between.

“ _Such a lovely face_ ,” he sang when you were looking at him, making you blush at the comment. “Heard me singing I suppose,” he said as you went to pour yourself a glass. 

“Good song,” you said as his hand grabbed the bottle first.

“Courtesy the Hotel California,” he said with an accent as he filled your glass. You laughed.

“I thought they didn’t have any wine,” you said as Dean reached across the table to cover your mouth as you chuckled.

“ _Such a lovely place, such a lovely face_ ,” he sang the lows and highs as he started to laugh, pouring himself a glass as well. You mumbled against his hand and he pulled it away.

“ _You can check out anytime you like but you can never leave_ ,” you sang. Dean gave you a devious look as he put the bottle down.

“You got any classes tomorrow?” he asked, picking up his fork. 

“Just turn in some papers but I’ll do that in the morning and then the day’s mine,” you said as you went to plunge some spaghetti in your mouth, stopping when you saw Dean still twiddling his fork. You thought something might be wrong until he lifted his head and looked up at you through his lashes, eyes soft and hard at the same time with one clear intention.

“Any plans until monday?” he asked, twirling his fork in the pasta, glancing at you with a look that shoot straight through you. You should have gotten yourself off when he was in the shower and now you didn’t know if could last through dinner.

“Have  _you_  got any plans until monday?” you said turning the question on him.

“I plan on doing one thing,” he said, his voice normal again.

“What?”

“You,” he said, his voice making your pussy tighten. “You’re still my dirty little girl, ya know, even if I am your good little boy,” he said lifting his fork to eat. Just hearing him call himself that made your stomach coil with want. You picked up your fork and began eating quickly, Dean doing the same but only because he was starving. You on the other hand, you had reached your free hand down into your underwear out of sight and were rubbing circles around your clit. If he could pull it off in front of his parents surely you could do it when it was just him.

“This is really good,” he said as you slurped down some of yours. His eyes were dark as he licked his lips.

“What?” you asked, taking another bite and slurping again. 

“You got some white sauce on your chin…almost looks like…well,” he said with a smirk as he leaned over the table to wipe your chin with his thumb. He sucked it off as you looked up at him, slightly astonished. “Doesn’t taste as good,” he said, glancing down and leaning back only an inch before coming back to lean over you, his head staring at your crotch. When he lifted it, his face was a mixture of surprise and desire.

“You getting yourself off right now dirty little girl?” he said, his face just inches from yours.

“So?” you said, resuming your motion, letting Dean watch as you did so. “You had no fucking idea,” you said as Dean pressed his forehead against yours. “Too busy imagining your cum on my chin.” His hand grabbed your wrist and pulled it out of your underwear making you whimper.

“Want to make a bet?” he asked and you scoffed.

“First time we made a bet, you cheated. Second time, I tried to cheat but you knew it somehow and you won. I don’t have the best track record with you,” you said as Dean released you and started cleaning up your dishes faster than you’d ever seen anyone before. When he was done, he grabbed you by the wrist and started pulling you towards your bedroom.

“Hey, I only suspected up until this point that you tried to cheat. Now I know…and you’ll get what’s coming to you for that,” he said, pulling you into your room and shutting the door.

“That’s not tonight?” you asked, somewhat disappointed. His hands were on your body, gently pulling you out of your clothes as you did the same to him until both of you stood there naked.

“Get on the bed,” he said and you did so, crawling over to the side you normally slept on as Dean sat across from you.

“Whoever gets off first loses. Winner gets to decide how we spend the next few days together,” he said as you felt yourself drip on the bed. You could see that he was getting harder by the second just thinking about it. “Permission for new things of course,” he said when you stayed quiet.

 “We can pick anything we want?” you asked, trying to keep yourself from getting turned on. 

“Yes, with permission,” he said, a glint in his eye. You held out your hand to shake his and after sealing the deal, you both watched each other carefully. You tried to focus on going slow, rubbing yourself gently but watching Dean stroke his tip so methodically was driving you nuts.

Dean’s hand started to pump over himself faster and you knew you were having the same affect on him. You shut your eyes so you wouldn’t see him work his cock, rub it, run his thumb over his slit that was leaking, dripping with precum. 

“Fuck,” you said as your pussy clenched at nothing, your pleasure passing that margin where you knew there was no turning back. You could feel your end, but fuck if you were losing to him again. 

Opening one eye, you saw Dean had his shut, and caught site of his hand running over his throbbing length. You shut it quickly as all you could hear was the sound of him fucking his own hand. 

“Y/N,” you heard Dean say. “You’ve got to stop moaning,” he said as you finally noticed the wanton sound that left your lips. You would have scolded him but hearing his voice full of need drew you closer to the edge and you dropped your head back, your clit ready to burst.

“No,” you whimpered as you forced yourself to hold off. It’d never been easy but when Dean told you, you could force yourself to listen to him. 

“Yes, do it, cum,” he said as you shot your eyes open. His were open as you tried to throw something angry his way but instead your eyes fluttered as you rubbed your clit harder, a laugh escaping your lips. Dean smiled as he moaned. You were both close, too close to that edge.

“You do it little boy,” you said and saw him have to physically fight to not cum right then and there. He tried to give you an equally angry glare but all you saw was pleasure and something else you couldn’t place.

“Fucking cum right now dirty little girl,” he said, his hand gliding over his cock fast and hard. 

“Cum for me good little boy. Fuckin’ cum all over me,” you said, urging him on as you ran harsh circles against your bud.

“Little girl,” he whined out.

“Little boy,” you breathed out.

“Cum for me, right fucking now,” he said, regaining all of the authority in his voice and then some. You exploded at his demand, your orgasm crashing over you as you screamed from the intensity of it.

Dean let out a long moan as you saw his cock twitch and his cum spew onto you and your bed, covering your body in it. Each one of you took a long time to come down and when you did, you were spent. You panted as you closed your eyes for a long moment and then opened them to find Dean had crawled closer to you.

“Sorry about the sheets,” he said, nothing sorry at all in his eyes.

“We can sleep at your place,” you said as Dean’s long fingers ran over the cum that painted your body. He brought his fingers to your lips and you greedily cleaned his taste off of him, humming as the salty mixture hit your tongue. Fuck you loved how he tasted. Dean ran his thumb over your chin.

“Whoops,” he said as he leaned in and licked off the one stray remnant that had made it on your face. “That’s better,” he said as he pulled back and then crashed his lips against yours. He was forceful but he wasn’t fighting you, both of you working together, having done it enough times to find that sweet spot for both of you.

“Such a lovely face,” you said when he broke away for air and you caught the smallest hint of a blush on his cheeks.

“Let’s get you cleaned up,” he said, hoping off the bed and picking you up in one fell swoop, carrying you into your shower. He smirked as you turned on the water and he got in besides you. “You know you lost. Again,” he said in your ear as your hands worked together to rid your body of him.

“Almost won,” you said as Dean’s lips found your neck and started to kiss you there as warm water rained down on the both of you. You reached your hands behind you, grabbing him by the hips and bringing him flush against you. Both of you were still sensitive so you were gentle when you reached behind your back, your hand finding his semi-hard shaft.

“So beautiful,” Dean mumbled against your neck as his fingers reached down to your pussy, slowly dipping one, then two, then three inside of you. It didn’t take long for him to stand fully erect once again, prodding into your backside. Dean’s finger’s left you and his hands roamed over your hips.

“I want you inside me,” you said over your shoulder. Dean brought his lips to yours and kissed you gently as his tip slipped into you, eliciting a moan from you. Dean smiled against you as he pushed in further. “Fuck, Dean. You feel so good,” you told him as you grabbed onto his hips, forcing him deeper into you.

He’d been in you before but it never felt like this, this tight, this good. He’d barely worked you over so your cunt was still wound up, still hoping for something to grab onto. Boy had you found it.

“Y/N,” Dean said as he twitched inside of you. He pulled out slow and moved back in even slower, letting you feel every glorious inch of him. You leaned your head back against his chest and let him set the pace. Normally you hated slow, only wanting it every few months. Yet here you were, only a few days from slow and Dean made you excited for the next time he would be this way with you.

“Where did I find you?” you said as you felt your walls clench him tighter, Dean’s cock spasming in you. 

“That’s my line,” he said with a laugh as he lowered his head to kiss your shoulders. 

“Good-” you got out as you went to praise him but felt yourself start to cum, the ability to speak leaving you.

“So-” you heard Dean say as his head dropped onto your shoulder, unable to praise you back, his cock shooting his cum inside you just as you clamped down on him. The movement of your walls fluttering around his length, squeezing everything they could from him prolonged your orgasms. 

Dean pulled himself from you slowly, his hand finding the shower head and turning the water warm once again. His large hands roamed over your body and it took you a moment to realize he’d opened your soap and was cleaning you up. Lifting your head off his shoulder, you turned to face him. 

Every time you saw him…he looked happier somehow, even when he was jealous, devious or mad, he was happier. He smiled as you ran your small hands over his muscles, cleaning the sweat and sex off of him as he did the same for you. Eventually you finished, neither of you saying a word as you enjoyed the content silence between the two of you. Dean stepped out into the hall to get towels to dry off.

“We can just sleep on the couch if you’re too tired to walk to the house,” he said. “Or I could carry you but I don’t think you’d let me,” he said as he shook the towel in his hair, making it stick out at odd angles when he moved the towel away. You stifled a laugh.

“I like your bed,” you said as you walked past him into your bedroom. “Let me pack something to sleep in,” you said as you climbed over to your clothes on the floor.

“I’ve got plenty of shirts,” he said and you stopped as you pulled on your jeans. You gave him a cocky smile as he saw that he had you.

“Fine,” you said feigning defeat. You loved sleeping in his shirts. “But I’m brining some pajama shorts,” you said, walking over to your dresser and tossing them in your backpack.

“You in a little pair of girly shorts? That might just be the cutest thing I ever heard,” he said, slipping back into his clothes by the time you pulled your shirt down over your face.

“What are you waiting for then?” you said, walking into your bathroom and shoving a few things in the pack so you wouldn’t have to rush back in the morning.

“Waitin’ on you sweetheart,” he said as you walked out of the bathroom and stopped, dropping your bag before walking into your room to find your bed already bare. 

“Did you…” you called out.

“In the washer. Your stuff and my clothes should be dry by morning,” he said from the front of your apartment.

“Oh frat boy,” you said, unable to keep a smile off your face.

“Come on, I can’t wait to get you back in bed,” said Dean as you put on your shoes. “Sleeping next to of course because I don’t know about you but I’m fucking beat.”

“Same,” you said, standing and waving him outside as you locked up. Both of you slung your packs on and started the ten minute walk to his place. “Dean?” you asked, watching as he turned to look down at you. “Since you won and everything, you got anything planned?”

“Yup,” he said, raising his eyebrows and nodding his head. “Bet you’d like to know,” he said with a look that told you he’d rather die than tell you.

“Just one hint?” you asked, putting on as innocent a face you could. Dean saw right through it.

“How do you feel about blindfolds?” he said and your heart started to race. “I’ll take that as yes,” he chuckled.

“So-”

“Shh, sweetheart. You’ll find out tomorrow,” he said, his hand bumping into yours. You saw someone walking on the other side of the street and grabbed Dean’s hand out of instinct. “Okay?” he asked, holding on tight so you wouldn’t let go.

“Yeah,” you said, glad he was there with you.

“Almost there,” said Dean. “Frat boy’s got you.”


	5. Chapter 5

**Summary for the Chapter:**

> Dean and reader take a weekend road trip…

When you heard Dean’s alarm clock, you realized he had curled up in a ball again, curling you with him as you slept.

“Shudyup would ya,” Dean mumbled as he reached behind himself to smack the thing off. Your back was to the ongoing action as you heard Dean grumble before finally making the sound stop. 

“Dean,” you said as you felt him tuck you in tighter as he nuzzled his head against the back of your neck. He mumbled, his lips touching the skin there, sending shockwaves through you. Once again his long legs fell over yours, making sure you wouldn’t move away.

“Just a few minutes,” he said, his voice quiet. You nodded against him, letting him hold you close. His chest rose and fell softly, the feeling of his steady heartbeat pounding through your back and straight into yours. You were positive he could feel yours as well, the sensation calming you. “Can we stay like this?” he whispered in your ear. Two different lines of thought hit you, both with differing answers as you went with the safer one.

“I’ve got to turn in my stuff, Dean. You can cuddle me all you want after that. We’ve got four days to just us…if you want,” you added, not wanting him to have to feel that he had to spend all his time with you. He had won after all, he got to pick what he wanted that weekend. 

Dean’s hand moved from your waist and up to your cheek, cupping it as he turned your head back to face him. He pressed his lips to yours softly, no need in the kiss, as his fingers gently stroked your now flush cheeks. 

“Why would I want to be with anyone else,” he said casually when he pulled away, his hand returning to it’s natural place around your waist. He tensed behind you for a moment before relaxing, a small sigh escaping his lips. You lay with him as you stared at the bottom of his window, the shade not having been pulled down all the way, letting a sliver of morning light spill into the otherwise dark room.

You held in a sigh you didn’t want him to feel. Once these four days were up, once it was Monday, you had to go back to sleeping on your own. He wanted you for sex, nothing more. Mornings like this, late night walks and talks with him, sleeping in his shirts…he was Frat Boy and he didn’t want that.

“Are you okay?’ he asked as you realized you’d been holding your breath.

“Mhm,” you mumbled back, moving your legs, Dean reluctantly releasing his hold on you. “Come on, let’s go have some breakfast,” you said, climbing out of his bed. You walked around it as Dean sat up, his hair messy, his chiseled features somehow soft in the morning light. His green eyes watched you carefully, his eyes roaming over your body, moving up your legs to your black cotton shorts, his gray tee, your bedhead that you tried to pat down as best you could. Nothing in the way he watched you was sexual.

“Are you sure? You’re not nervous or anything about what I have planned? I was just joking about the blindfold if that freaked you out,” he said as he swung his legs out of the bed and walked over to where you stood. You stared up into his concerned looking eyes. Fuck, he was convincing. He was your friend. You were okay calling him that. Anything further and you were just lying to yourself.

“I’m fine Dean, really,” you said, giving him a reassuring smile. He narrowed his eyes before relaxing.

“Alright,” he said, moving his hand to the small of your back, leading you towards the door. “I’m here to talk if you decide you’re not.”

You smiled again as you opened his door and stepped out into the hall, Dean keeping his hand on you as you walked towards the stairs. He dropped it when you took a step down and thought you felt him brush your hand but when you rounded the corner to head down to the first floor, he was running his hand through his hair. You caught him part his lips like he was about to say something but then he shut them, obviously deciding against doing such a thing.

“Morning guys,” said Sam when the two of you walked into the frat’s kitchen. You were amazed at how clean it was when there wasn’t a party going on. “Cereal?” he asked, holding up a box from the table where Cas, Gabe and Chuck, at least you thought that was his name, sat with him.

Dean moved to a cupboard and pulled out two bowls for you, opening up a drawer and grabbing some spoons as well, while you took an empty seat besides Gabe.

“So, Y/N, how the hell do you get him out of bed? We’ve never seen him out of here on time until you started hanging out with him,” said Gabe as Dean placed a bowl in front of you and began filling it with cereal.

“No idea really. The guy loves to cuddle. I’m surprised he actually listens to me,” you said absentmindedly as Dean poured milk in your bowl. When you looked up you realized your mistake. Dean’s face was red from embarrassment while the others were biting back laughter. 

“Wow…” said Chuck, a wide grin on his face. Dean sat next to you and kept his head down as the others started to let their giggles slip from their lips.

“Thanks for that, Y/N,” said Dean in a low voice as he played with his spoon. 

“Why the hell are you laughing at him?” you asked, trying to put some force into your words. “Like none of you like cuddling,” you said with a scoff. You brought a spoonful of food to your mouth as you looked around the table. Four faces looked a little ashamed, one had a small smile.

“Always knew he’d get a feisty one,” said Sam with a smile. You put your head down as you ate. You weren’t his, you just didn’t like his friends making fun of him for doing something…so natural.

“You coming with us to the football game Saturday?” said Cas, trying to ease the tension in the room. You looked at Dean uncertain.

“We’ve got other plans. Next weekend?” said Dean to Cas as the four brothers watched him with goofy smiles.

“Did you beat him in pool?” asked Gabe. “Is that why he’s so…”

“I’m not answering that question Gabriel,” you said as Dean chuckled. 

“Let her eat in peace, dude,” said Dean, giving him a friendly but cautious smile. Gabe nodded and let it go thankfully. You wouldn’t be able to explain your situation with Dean, even if you tried.

“I’m going to get dressed,” you said, standing from the table. “You want to meet me at my place later or…?” you trailed off as Dean started shaking his head.

“I was going to walk with you while you dropped off your stuff,” he said, standing as well. “Is that okay?” he asked, picking up your empty dishes. You hummed in response as Dean placed the bowls in the sink. The young men at the table stared incredulously at Dean and then at you. You shrugged at them as they turned their attention to one another, each one raising their eyebrows. You turned away and started walking out of the room, Dean hot on your tail as he saw you were no longer with him.

“Are you sure you’re okay this morning?” he asked from behind you. You rolled your eyes when he couldn’t see your face.

“I don’t need a babysitter, Dean,” you said as you headed up the stairs. “It’s 8:30 in the morning, you’re on campus, there’s no psycho’s out there that are going to grab me in the 100 feet walk to the quad,” you said, exasperation on your words. Dean was quiet behind you as the two of you walked up the stairs and back to his room. It wasn’t until he shut the door behind you that he spoke.

“I like walking with you and I thought you liked it too, that it made you feel safe. If it makes you uncomfortable-”

“No, that’s not it…I don’t want you to feel like I expect you to walk me places, that I’m expecting you to do certain things for me like pour me cereal,” you said, rubbing your arm. Dean looked at you confused.

“I don’t feel like you expect me to do anything except fuck you on occasion. I like doing those other things, that’s why I do them, not because I feel like I have to,” he said. You could feel that the room was starting to become tense.

“I just wanted to make sure,” you said with a smile. “That’s what was bugging me this morning. But as long as you’re happy then it’s all good,” you said, trying to sound as genuine as possible. Dean appeared to buy it as he instantly smiled at you.

“I’ll let you…get ready,” he said waving towards the bathroom. “I’ll be downstairs in the front room when you’re ready to go,” he said, walking over to his dresser and pulling out some clean clothes. You pulled your backpack into the bathroom and gave him a small wave.

“See you soon.”

 

When you skipped down the last few steps, you spotted the back of Dean’s head as he sat on the couch. You saw how the short hairs curled into a cowlick on the back of his head and couldn’t keep the smirk off your face. It was such a boyish thing to see on a man, especially one like Dean.

“Ready,” you said and saw him turn around instantly. He hopped off the couch and followed you out the door and down the few steps to the sidewalk. He was quiet as he let you lead the way, first to your history professor’s office, then your english one.

“You all done?” he asked as you came back into the hall.

“Weekend’s ours,” you said to him and caught his smirk. You were sure he had plenty planned for you.

“Good,” he said, walking over to you and heading towards the exit. That was until you saw Nick step out from his office.

“I thought I heard you two,” he said. “Dean, you did very well on your test, best in the class.”

“Thanks, Nick,” said Dean as he pressed his body close to yours. Nick noticed the movement as he turned to you.

“Y/N, have you thought any more about the TA position?” asked Nick. You were about to mess with Dean, just to rile him up when you felt his hand squeeze your ass, out of view of Nick. 

“N-n-no. I, uh, next semester’s a little too busy for me, sorry,” you said as you felt Dean’s hand on you again. Nick looked disappointed.

“Well my door’s always open, you guys have a good weekend,” he said, returning to his office. You walked forward as your breath hitched in your throat, opening the door to the stair well when Dean grabbed your arm. He waited for the door to close and listened to make sure you were alone.

“Good girl,” he said in your ear. “You were going to fuck with me again, weren’t you?”

“Yes,” you said, looking up at him through your lashes. “But I didn’t.” Dean gave you a coy smile.

“Because you know who you belong to,” he said, his voice ragged. You swallowed thickly as you reached your hand down, lightly touching him through his jeans, causing him to buck his hips up.

“And you know who you belong to,” you said, Dean letting go of your arm. He licked his lips as he took a step down the stairs.

“Well now that we know who owns who, why don’t we start this weekend,” he said, motioning for you to follow. You got down to the bottom and stepped outside in the early morning air as Dean fished a hand into his pocket. “Here,” he said, handing you a folded up piece of paper.

“What’s this?” you asked, unfolding it. 

“Everything you need to pack and whatever else you want to bring. We’re taking a road trip,” he said, walking towards the direction of your house. You followed after as he waited for you so you could walk side by side.

“Where are we going?” you asked. Dean put a finger to your lips. 

“It’s a surprise. But it’s nice and private. We can be as loud as we want,” he said. “I think you’ll enjoy it…hope you’ll enjoy it,” he said, staring at his feet as he walked. You reached out and took his hand in yours, swinging it slightly.

“I’m sure I’ll love it,” you said as you felt him intertwine his fingers with yours. He walked with you back to your apartment, his hand squeezing yours whenever you had to cross a street or when he caught a few guys from a different frat eye you up and down.

“Perverts,” he muttered under his breath after you passed them. You used your free hand to wrap around his arm.

“They were just looking, Dean,” you said as you felt his bicep tense under your hand.

“Well they shouldn’t look at you like you’re a piece of meat to be devoured,” he said, stopping at the intersection by your place. As you stood there waiting for the light to let you walk, you gave his shirt a tug.

“Because that’s your job,” you said with a giggle. Dean rolled his eyes which surprised you.

“Because you’re a person, Y/N,” he said as he looked both ways before stepping off the curb. “The fact that it’s my job is besides the point,” he said, the edge out of his voice now.

“Can I get pissed at girls that look at you then?” you asked as you crossed the road and stepped onto the sidewalk. Dean smiled wickedly.

“You and jealously would make for a very dangerous combination I suspect. Not that it wouldn’t be fun for me,” he said as you spotted your apartment just a ways down.

“Oh really?” you said, letting go of his hand so you could find your keys in your pocket.

“I’m pretty sure I’d be getting a call from you to help hide a body,” he said, leading you up the steps to your door. You scoffed.

“Well would you?” you asked, pulling a laugh from Dean.

“Anything for my sweetheart,” he said, a flutter occurring in your heart. “I just think you’re very protective of what’s yours is all,” he said as you opened your door. You nodded.

“Yes I am my good little boy,” you said, facing him with a smirk. You saw the small shudder that ran through Dean’s body at your words. “Oh, I’m going to have so much fun with you this weekend,” you said, letting your eyes roam over him.

“In your dreams little girl,” he said with a wink. “I’ll be back in an hour or so to pick you up, okay?” he said with a soft smile. You nodded your head in response as he leaned down and pressed a quick kiss to your cheek before dashing down the steps and towards the frat house.

“He’s not…” you trailed off, speaking to your empty apartment. “Fuck, why does he have to be so…” you trailed off again, throwing your arms about. “I’ll deal with this Monday. We’re having fun this weekend and that’s all that matters,” you said, deciding to put the issue at rest until after your weekend excursion. 

 

An hour later you heard a knock on your door as you sat up from your couch. You had emptied out your backpack and filled it with the things Dean asked for, using a spare duffel you had laying around for the rest. He’d asked you to bring simple things like jeans and shorts, t-shirts and long sleeves, pajamas and a hoodie, a bathing suit and jacket, flip flops and a pair of shoes you didn’t mind getting dirty. You honestly had no idea where the hell he was taking you and you thought that might have been the point.

“You all set?” he asked, leaned against the doorframe when you opened it. He looked relaxed in his standard look, a red shirt paired with a black tee and jeans. He had a pair of sunglasses on top of his head. You looked down at your jeans and tank top you had on, opting to slip on a pair of sneakers. 

“You going to tell me where we’re going yet?” you asked as Dean stepped inside and grabbed your bags for you. 

“Nope,” he said, grinning at you as he turned back out your door. You locked up behind him and watched him hop down the steps again when you caught sight of his car.

“Oh baby,” you said, walking over to the muscle car quickly. Of course he had a badass car.

“How’d you know her name?” he said with a chuckle as he put your bags in the trunk besides his.

“Lucky guess,” you said, walking to the passenger side. Dean stopped at the driver’s side before turning to look at you. “You know my mother always said never to get in a car with a strange man,” you said, opening the door and sliding onto the bench seat. Dean opened his and slid in besides you, pulling it shut at the same time as you.

“I agree with her, you should really only get in cars with a frat boy,” he said giving you a cocky smile.

“Oh, so those guys from before are okay now?” you asked coyly. Dean gave you a dangerous smile.

“I said Frat Boy, sweetheart. That’s me in case you forgot,” he said, leaning over, just inches from your face. You leaned forward, closing the gap between you so that your lips just brushed his.

“Well she never said anything about you,” you said, feeling the breath escape his mouth before you pulled back, denying him the opportunity to kiss you. He shook his head at you as he moved back, turning the key in the ignition.

“You are such a tease,” he said, putting on his blinker and turning onto the road. You caught him smile at you every so often as he turned up the radio, your hair wiping in the wind with the windows rolled down. 

It wasn’t long before you were off campus and on the highway. You were headed north but that’s all you knew. You stuck a hand out the window as you heard Dean start singing to himself. Normally you hated when other people heard you sing, mostly because you were awful, but Dean wasn’t great either and soon you found yourself singing along with him.

You felt his right hand reach around your shoulders as you belted out the chorus and made up the words you didn’t know. For the next two hours you listened and talked. He asked you stupid things like your favorite color and where you were from. You asked him what his favorite book was and saw him blush just so. 

“How do-”

“Last Saturday, when I came in your room, you were reading. At first I thought you were trying to impress me but you have too many in that room of yours to try to be showing off. It’s okay ya know. I like smart guys,” you said, lightly shoving his shoulder. He bit his lip and kept his eyes on the road in front of him.

“You mind if we stop at the next rest stop?” he asked and you hummed in response. A few miles later, you pulled off and used the restroom, buying some snacks for the two of you while Dean disappeared. When you walked back out to the car, Baby you supposed it was called, you saw Dean shutting the trunk, holding something behind his back.

“You said you like salt & vinegar,” you said, tossing him a pack of chips. He caught it with one hand, holding the other behind his back. He ripped it open with his mouth.

“You trying to see what I’ve got back there?” he said, shoving his hand in his pocket and pulling it back out empty handed. Whatever it was, it wasn’t very large.

“Maybe,” you said as you leaned against the car besides him, eating a candy bar. Between bites you saw Dean’s head bob down and bite off a piece. You scoffed at him but saw he had put on his innocent puppy dog eyes.

“Am I in trouble?” he asked, licking the salt off his lips. You raised your eyebrows as you reached into his bag and pulled out a chip.

“Depends,” you said, scarffing it down and taking another bite of your chocolate. Dean grabbed the remaining piece and popped it in his mouth before you could stop him.

“Depends on what,” he said, tossing the wrapper and his in a nearby trash can.

“Depends on whether you want to be in trouble,” you said, placing your hands on your hips. He placed his hands on top of yours, moving you closer to him.

“Hmm, now why would I want to do that,” he said, leaning down. You stared into his eyes, waiting for him to come closer to kiss you when his hands left yours and started running up and down your sides.

“Dean!” you squealed, his tickling making you laugh. He started laughing as well but for different reasons.

“More? If you insist, Y/N,” he said, his fingers running over your body so that you had curled up against Baby, completely at his mercy.

“You are in so much trouble!” you got out between giggles before Dean finally relented.

“I guess that sucks for me,” he said with a shrug and a devious smile. He waved you into the car and you climbed back in, watching him do the same.

“You know, if you want me to be in charge, you could just ask like a big boy,” you said as he turned the car back on.

“Sorry, you’ll just have to teach me to be a good little boy,” he said as he fished his hand back into his pocket. You gave him a sly smile.

“Oh, I’ll teach you alright,” you said and you could have sworn you saw Dean part his lips at your promise. He grunted and you knew he was turned on.

“On the subject of teaching, you may have admitted to trying to cheat in our little bet if I recall correctly,” he said, placing his hands on your shoulders and gently turning you to face away from him. Your heart raced as his fingers danced along your skin.

“What are you gonna do about it,” you said, egging him on. His hands trailed over your neck, lightly moving up and down.

“Punish you obviously,” he said, his voice rough in your ear. You felt a twinge run through you. It didn’t matter if he was putty in your hands or the man in charge, he still turned you on like no one else ever could. “And you know how I’m going to do that?” he asked. You shook your head besides him.

“No,” you said as you felt him move his hands away from you, still hiding whatever was in his palm. You turned around to see him take the car out of park.

“You’re going to have to wait to find out,” he said, putting his hand back in his pocket and coming out empty handed. You groaned and a satisfied chuckle erupted from Dean.

“You realize I’m counting this towards your punishment,” you said as he pulled back on the highway.

“Oh I hope so,” he said, turning the radio back on as you continued on the road.

 

You’d stopped for dinner a while ago and had driven right into rain. Of course Dean had to get a flat and change it on the side of the road as the sun was going down. You offered to help but he told you to stay in the car. You did as he asked and you were headed towards your destination a few hours later. It was night now and Dean had turned the radio off. He’d pulled off the highway some time ago but you had no clue where you were. The only light you saw was from the dash and the headlights, nothing more showing up. 

You made the mistake of leaning your head against the window as Dean talked, his voice soothing you to sleep like a lullaby. It didn’t take long for you to pass out. You felt yourself wake as the car came to a stop. You cracked open an eye to see a small, but nice looking house in front of you. You felt the trunk slam shut as Dean came into view carrying all four of your bags, holding a pair of keys in his free hand. He opened the door and placed the bags inside, flipping on a light before coming back out.

You let out a long yawn and lifted your head off the window, closing your eyes again. You felt the driver’s side door open and the engine turn off. 

“We’re here,” Dean whispered as he opened up your door and you felt him place a strong arm under your knees and one behind your back. In a second he had picked you up and lifted you out of the car, kicking the door shut behind him.

“I can walk,” you said sleepily as you let yourself lean into him. His grip on you tightened as he carried you into the house, your eyes half open. When you got inside, it was dark for the most part but it looked clean and cozy in there. Dean carried you to a partially open door and pressed against it with his back. He walked forward until you felt him put you down on something soft, a bed you imagined.

He left the room as you heard him shut the front door and carry your bags into the bedroom you were in. He turned on a small light in the corner before moving back over to you.

“Didn’t mean to get us here so late,” he said, taking your shoes off of your feet. You didn’t realize you even had them on. 

“S’kay,” you mumbled. You felt Dean’s hands undo your jeans and tug them off your legs. “What wanna do,” you mumbled again as you tried to sit up, wake yourself up for whatever he had planned. Instead, you found a large hand push you back down.

“I want you to go to bed sleepy,” he said, placing your jeans and shoes near your bags. You reached behind yourself and undid your bra, removing it and holding it up. Dean took it and put it with your other things. “We’ve got time for the other stuff all weekend,” he said, pressing a kiss to your forehead.

“’Kay,” you said as Dean lifted your legs up so he could help you get under the covers. You rubbed your bare arms and soon felt a heavy blanket be draped on top of the bed, making sure you’d be warm. You heard Dean shuffle around a little before the light clicked off and Dean climbed in next to you. 

“G’night,” you said as you turned to throw an arm around him, getting close to him. Dean seemed a little hesitant at first, he was always the big spoon, but his hand wrapped over yours and you knew he was happy with letting you hold him.

“Goodnight, Y/N,” he said. You heard him mumble something else but you couldn’t make it out, sleep overcoming you quickly in the comfortable warm space.

 

“Morning beautiful,” said Dean when the two of you finally woke up. You opened your eyes to find Dean had reclaimed his natural position of curling you up in him.

“Morning,” you said, turning your head so you see his face. “Guess what?” you said and Dean raised his eyebrows. “No alarm clock,” you said and saw a smile spread over his lips.

“That thing really does get in the way of me doing this,” he said, his legs falling over yours, trapping you. “No excuse to get out of bed today,” he said and for once, he was right. He didn’t need to make sure you weren’t going anywhere because you didn’t want to go anywhere. 

“Hmm?” you hummed as you opened your eyes to discover Dean was simply holding you now, his legs back behind yours.

“You fell asleep for about half an hour,” he said and you sighed against him. “It’s okay, I like watching you sleep…and that sounded super creepy,” he said as he let go of you. You turned your body around to face his, placing a hand on his chest.

“You’re cute when you sleep,” you said, running your hand up and down his chest before he eventually caught your wrist. His eyes told you he had other plans.

“Later,” he said, holding your hand in his. “Let’s have some fun first,” he said, sitting up  and using his free hand to bring you up with him. He held both your hands in his as you pouted.

“But that’s fun,” you said, looking down at his boxers and back into his eyes. It took you a second to realize what was hidden in them as he moved his hands to your wrists and you saw his eyes flicker down to them briefly. “Shit,” you said as Dean took both of your small wrists in one of his hands. You gave them a tug but no way in hell were you getting out.

“My dirty little girl,” he said cocking an eyebrow and throwing you a dark smile. He leaned over the bed, pulling you onto your knees as he dug around in the bedside drawer. “I know you’re curious about what was in my pocket…” he said, pulling out a single piece of strong silk fabric. A blindfold. You felt yourself start dripping just at the sight.

“Fuck me,” you said, as Dean dangled the silk in your face. 

“I plan on it sweetheart. If you don’t want to do this-”

“I trust you,” you said, his green eyes afraid he was pushing you too far. “Go ahead,” you said and on cue, Dean released your hands, nodding his head.

“You’ll tell me to stop if you don’t want to keep going,” he said and you pulled off your shirt, leaving you in nothing but your underwear.

“Of course. Now are you going to use that thing or what,” you said, sitting up on your knees so you could look down at him. He nodded one more time before his trepidations left him and he stood, something dark replaced in them.

“Underwear off,” he ordered, his voice suddenly much rougher. You did as he asked and flung them at him, swinging your hips as you sat on your knees again. “Bad girl,” he said, catching them, feeling how wet they were.

“I was promised a punishment, Winchester. Time for you to walk the walk,” you said, reaching out a hand and running a finger down his chest. Even though a shirt separated you from his body underneath, you couldn’t help but feel the way his muscles rippled under your touch.

“Be careful what you ask for,” he said, snapping the fabric. “Turn around,” he said. You faced away from him as you heard him begin to take off his shirt and boxers. “Close your eyes,” he said as he held one end of the fabric in each hand, bringing it down in front of your face and resting his hands on your shoulders. You shut them and felt his hands move off of you.

The silk brushed your cheeks as he placed the soft material over your eyes, pulling it taught and tying it behind your head. You bit your lip to stifle a moan. He hadn’t even touched you and you were already a mess for him.

“Open you eyes,” he said and when you did, you were met with darkness. You tried to glance down but there was absolutely nothing. You were completely blind.

“I can’t see anything,” you said, a little timidness coming through in your voice. 

“Feeling helpless?” he asked, running a finger against your cheek as you leaned into his touch. You weren’t going to last long like this, his touches feeling magnified by a thousand now that you couldn’t see them coming.

“Yes but in a good way,” you said, trying to reassure him that you were still okay, more than okay, with how this was going. His lips trailed down your neck as you felt him crawl on the bed behind you, moving you forward some as he placed his hands on your hips. You kept your hands by your sides, balled up into fists, not sure if he was going to let you touch him.

“How do I make such a dirty little girl into a good one,” he said, running his hands up and down your arms. You dropped your head, his hands on your body doing sinful things to you. “Any ideas?” he asked, his hands coming off your arms and onto your hips, slowly sliding up the sides of your body until you felt them touch the bottom of your breasts. “Keep your hands in the sheets until I say, okay sweetheart?” he said and you nodded against him.

“Dean,” you moaned as hands started to slowly knead the soft flesh, his long fingers working your nipples. You lifted up your head just to drop it back against his chest, arching your back so that he knew you were enjoying yourself. You felt him shift behind you and then you let out a strangled whimper as Dean took one of your nipples in his mouth.

He hummed against you, his tongue licking at the bud, his teeth nipping at it, tugging ever so slightly as you fisted your hands into the sheets. As he did all that, his hand worked over your other breast, the nipple hardening under his touch. Dean sucked hard on the nipple in his mouth before popping off, quickly latching onto the other one and giving it the same treatment. His hand worked the other one again, both sensations sending you reeling.

Your pussy was screaming for attention and you oh so desperately wanted to rub your legs together, but Dean knew better than that. He had his legs between yours as the two of you kneeled on the bed, no possible way for you to bring them any closer together. 

“You feel how hard you make me? Feel how hard I get when you make those sounds, when I touch that gorgeous body?” he said, pulling away from you completely and pressing his length against your lower back. You felt him spin you around so that you were now facing him. You licked your lips, expecting him to bring the tip of his cock to them but instead you found something else. Soft flesh that tasted like a stolen candy bar. 

Dean’s lips moved with yours, opening your mouth so he could invade it with his tongue. You ran yours along the top of his experimentally and pulled a deep groan from him, a hand on the small of your back encouraging you to do it again. You did, allowing him to take control and tell you when he wanted you to take over. After what seemed like minutes, he pulled away panting. You dropped on your knees, your head down, trying to catch the breath you didn’t know you were missing.

“Please touch me,” he said, his hands lifting yours from the sheets and guiding them towards his body. Carefully, you ran your hands up his chest until you found his shoulders and then his head, wrapping your hands in the back of his hair.

“You,” you said, pulling him close to you, trying to kiss him but missing and hitting the bottom of his chin, his lips pulling up into a smile against you.

“You what?” he said, his lips finding yours and giving you the kiss you had been searching for. 

“I…” you trailed off as Dean pulled you onto his lap, his cock pressed against your abdomen, smearing some of the leaking precum on it.

“Do you want to stop?” he asked, backing away so you slid off and reaching up to undo your blindfold.

“Dean, I’m okay,” you said, your hands on either one of his arms before he could pull the thing off of you. “I just…I want you,” you said, Dean’s hands resting on your shoulders before pulling you back onto his lap.

“You’re lucky I’m in a forgiving mood this morning,” he said, his cock teasing your folds. “I could really torture you if I wanted,” he said, rubbing the tip of it against your clit, your body reacting easily under his touch. “But you couldn’t even pull off the cheat, now that’s just sad,” he said, his cock rubbing against your clit, your hands fisted into his hair.

“Please,” you begged, pressing your forehead against his chest. “I need you,” you said, your clit ready to pop then and there.

“Only because you asked so nicely,” he said, his cock dipping through your folds, his tip finding your pussy and pressing in slowly but firmly. You thought you’d taken him all when Dean gave a sudden thrust and you moaned loudly.

Your walls clenched around him, his tip pressed against your g-spot, his cock feeling larger than ever as it sat sheathed within you. Dean’s hands were on your hips and slowly helped raise you off of him until only his swollen tip was inside you. You tried to move back down on him but his hands held you firm preventing you from doing so. 

“Dean,” you groaned, wanting him to fuck you. Without warning, he pulled down on your hips hard, forcing him deep within you as you laughed and moaned at the same time. “Don’t stop doing that,” you said, all clear thought leaving your head from the one single action.

Again you felt Dean raise you up and you waited for him, his hands pulling you down without warning, your pussy quivering with each drop down onto him. From the sounds Dean was making, he was loving it just as much.

“Fuck, you love getting fucked by this cock. You love riding my huge cock, don’t you dirty little girl?” he said as he moved his hands quicker now, bottoming out in you each time you dropped onto him. 

“Yes,” you said with whine, your head fallen back now. “I’m your dirty little girl,” you moaned out as his cock throbbed violently within you.

“You want to cum?” he asked roughly, his fingers digging into your skin.

“Yes, please,” you begged, your pussy walls fluttering dangerously around his pulsating cock.

“Please what?” he said, biting your shoulder just enough to leave a mark.

“Please daddy, I want to cum,” you said without thinking. Dean slammed you down hard, harder than before and you screamed out his name, his cock so tight in you as it throbbed and you felt his cum splash your walls, some of it dripping out before you’d even started to come down yet. 

You held onto Dean for dear life as he rocked his hips, easing you down from your simultaneous highs before pulling from you.

“Taste you please,” you said, feeling his cum dripping out of your pussy. Dean chuckled as he placed two fingers along your folds, collecting what had come out before thrusting his fingers inside of you and running against your walls, one, two, three times before finally pulling from you.

“Open up sweetheart,” he said and you opened your mouth. Dean placed his fingers inside and you closed your lips around him. God he’d gotten so much cum, the salty taste heavenly as he slowly pulled his fingers from your mouth. When they were finally gone, you swallowed his cum, savoring the taste. You felt a hand behind your head and then everything was bright, your blindfold gone. When your eyes adjusted to the light again, you saw a satisfied looking Dean sitting before you.

“That was amazing,” you said, a huge smile on your face. Dean gave you one in return as he turned it into a smirk.

“Did you call me daddy there sweetheart?” he asked, already knowing the answer. You glanced away slightly embarrassed but Dean’s hand caught your chin. “Because that was such a fucking turn on,” he said and you smiled.

“I’ll make sure to do it again then,” you said, Dean’s hand brushing your hair out of your face. He stared into your eyes for a while but you weren’t uncomfortable.

“You want to get cleaned up and have some fun before we have some more fun again tonight?” he asked. You rolled off the bed and stood, waiting for him to take the lead.

“Anything for you Frat Boy,” you said with a wink. Dean rolled his eyes as he stood and led you over to an adjacent bathroom.

“That’s my line…again,” he said, leaning against the doorframe as you stepped into the shower.

“Anything for you…daddy,” you said, cocking an eyebrow and curling up your lips. Dean groaned and you saw his cock twitch at your words.

“Down girl. Daddy will take care of you tonight,” he said as he turned to leave you.

“Maybe he will after I teach someone how to be a good little boy. I’m not going as easy on you as you did just now,” you said, catching his attention.

“Oh I hope not,” he said, giving you one last smile before pulling the door shut to give you some privacy.


	6. Chapter 6

**Summary for the Chapter:**

> Dean and reader continue their weekend getaway…

“Um, you’re evil, you know that right?” you said as you sat on a barstool at the kitchen counter. Dean was standing on the other side, in a white muscle tank and salmon colored swim trunks. He just hummed as he gave you a smirk, watching you squirm. “Come on,” you whined, putting on puppy dog eyes.

“Y/N, don’t beg. It’s unbecoming of you. You know I  _hate_  it when you beg,” he said, his lips curled up into a full smile now. You rolled your eyes back and groaned. “Frat boy’s going to take care of you, just one more minute,” he said as you humphed. You crossed your arms over your chest, waiting impatiently. You scratched your bare arm, glancing down at the outfit Dean had asked you to wear this morning. A white tank top for you as well, a pair of loose black shorts and your bathing suit underneath. You’d packed your black one with the little strings, one tied behind your neck, one behind your back. Your bottom piece had them too on the sides. You hoped at some point in the day Dean’s hands would find their way to them and tug on one until it came loose.

“But..” you said as Dean cocked his eyebrows and waved a finger at you. 

“Patience is a virtue sweetheart,” he said as he turned around back to the griddle and placed a few pancakes on a plate. He did the same for himself before sliding the plate across the counter to you. “Enjoy,” he said as picked up the bottle of syrup and dumped nearly half of it on his breakfast.

“You know you’re going to pay for all of this later, right?” you said, a glint in your eye. Dean only smiled as he took a bit of food.

“I’ve seen what your punishment to your good little boy is like. I think I can handle it,” he said, his eyes testing you. You laughed.

“You know how good it felt to cum the other night, my hips just grinding against you?” you asked as Dean wolfed down another piece, syrup spilling out of the corner of his mouth.

“That all you got?” he said confidently, his eyes dark. It wasn’t quite what they looked like when he was turned on but it was close. 

“You shouldn’t have done that,” you said, looking down at your plate, hiding your wicked smile.

“Done what?” he scoffed. You looked up and saw him gulp when he saw your face.

“Told me what you wanted,” you said, finishing your second pancake. Dean pushed his plate away as he hopped up on the counter behind him, looking at you, trying to play innocent.

“I didn’t tell you anything,” he said, his hands, gripping the counter beneath him. You made sure he was watching as you let your eyes trail up his body slowly, closing them before opening them to stare him down. His lips parted when he saw the look in your eyes, that look you knew would drive him nuts. While you much preferred to let him be in charge, it didn’t mean you weren’t going to enjoy yourself letting him squirm.

“Yes you did good little boy. Now, pick a number,” you said, letting your eyes and voice become authoritative. 

“Three,” said Dean quickly, a small tremble of fear and excitement in his voice.

“That’s what I was thinking,” you said, finishing your food. “After lunch,” you said and he nodded. You didn’t want to spoil his morning plans.

“Well I’ve got a few hours to get in much trouble as possible then,” he said, hopping off the counter. You swung your legs off the stool and hopped on the ground as Dean grabbed your dishes and tossed them in the sink before turning and unplugging the griddle. You waited for him as he put the syrup away, glancing out the back doors. He’d taken you to the Winchester’s hunting cabin, even if they didn’t use it for hunting anymore. There was a lake out back with a diving platform out in the water, a canoe pulled up on shore from where you could see as well.

Your thoughts came back to Dean as something slimy touched your lips, Dean’s finger running over them. You backed up at it as you saw Dean holding the bottle of syrup and a childish smile. You were about to chide him when he brought his lips to yours, his tongue gliding over the flesh, tasting the maple flavor. 

“Yummy,” he said when he finished, You raised your eyebrows when he ran his finger in the hollow of your neck, leaving a small pool of the substance there. He brought his lips down and sucked on the spot, his tongue tickling your skin. You bit back a moan, tasting the residue of syrup and Dean. You weren’t going to give him what he wanted, let him know you were loving it. Not until after you’d shown him you could turn him into a whimpering mess like he did to you. Or tried to.

“Got to try harder than that Frat boy,” you said as he finally pulled away. He feigned a sigh as he moved to place the bottle back in the fridge, licking his own finger until it was clean.

“Fine. But if you fall out of the boat, or get pushed off the dock, I can’t say I didn’t warn you,” he said, walking towards the back door, grabbing a waterproof radio on the way. You walked with him outside and even though it was fall and you were in the woods, it was pleasantly warm on the sunny day. You followed him down to the water’s edge where he shed his shirt. You pulled off your tank and shorts, each of you taking the other in. “You are quite beautiful,” he said quietly, holding out a hand.

“You’re quite handsome,” you said, holding out yours. He moved to grab it before moving quicker, his strong hand pushing against your back, forcing you forward. You yelped at the sudden motion as you fell into the water, the lake bed dropping off quite deep off the small dock you had walked on. “Dean!” you yelled as you came back above the water, the chill of it shooting through you as you adjusted to the temperature. He stood there with a cocky grin.

“Whoops,” he said, nodding his head and shrugging his shoulders, his eyes mischievous. You attempted to splash some water on him but he was already jumping in the air, tucked in a ball with the radio in hand. You yelped again as Dean landed next to you, drenching you in water.

“Dean Winchester!” you said loudly when his head emerged from the water. He smiled even larger now.

“Last name? I must be in trouble,” he said with a wink as he started swimming over to the platform in the water. You followed after, Dean grabbing you by one arm and pulling you up onto it effortlessly when you got there. He turned on the radio and hoped back in the water as you sat on the edge, your feet dangling in the water.

“You look happy,” you said as he swam in small circles in front of you. He laughed.

“I am happy. I’m at my favorite place in the world with my fav- with you,” he said, cutting himself off mid sentence, a small smile settling on his face. You kicked your feet in the water, letting a smile fall onto yours.

“Thanks for inviting me. It’s nice here,” you said, Dean coming to rest his arms against the dock, looking up at you as he stilled in the water.

“You’re welcome. I can be myself here,” he said, resting his head on his arms, his gaze on you.

“And what’s being yourself?” you asked. You’d gotten to know Dean better, the real Dean, over the past few days but you still felt like he was keeping some part of himself hidden away from you.

“I don’t know. I don’t feel like I have to be anyone but me, ya know?” he said. You nodded in understanding as you rubbed the top of his head. He shut his eyes, his lips stuck in a permanent smile. “I like you. I’m glad you’re my friend,” he mumbled and you chuckled.

“I like you too, Dean,” you said, enjoying the moment. A song ended and one you hated turned on. Apparently Dean didn’t like it either as he asked you to change the station. You pulled up your legs and swiveled on your butt, leaning over to give Dean the perfect view of your almost bare back as you switched it.

“What’s that?” he said, absentmindedly reaching out to touch your back, just above your bottoms, behind your right hip. There was a scar there you’d forgotten he’d never seen, never would have noticed unless he was that close to you. You straightened at his touch and spun around.

“Nothing,” you said a little too quickly as Dean pulled his hand back. 

“Sorry,” he said. “I shouldn’t have…”

“It’s okay. I like when you touch me,” you reassured him. He squinted his eyes before looking down at the wood dock.

“So what-”

“I’ll tell you…but not right now. A different time. Now you going to pull me in the water and misbehave or what?” you said, shoving his arm lightly. Dean’s demeanor shifted back to being playful as he quickly wrapped his hand around your wrist. In a flash he was tugging on you, pulling you into the water.

“You asked for it sweetheart,” he said when you splashed him with water. “Y/N!” he laughed as he started throwing it on you. 

That was how you spent the next few hours. Swimming, playing, relaxing on the dock, listening to music and each other. Your face had started to hurt you’d never smiled that much. It’d been so long since you’d felt that happy you forgot what it felt like.

You insisted on making lunch despite Dean’s protests. You were his guest but you were going to pitch in. You brought out a few sandwiches and drinks to the deck off the back of the house, sitting at the table besides Dean. He wrapped a fresh towel around you as you ate lunch together. You ate yours quickly while Dean took his time. You lay your towel out on the grass and let yourself warm up in the sun, turning your head to see Dean watching you as he ate the last of his food.

“I thought you were going to do things to me, Y/N,” he said, wiping his hands together. You hummed as you beckoned him over to you. He walked over and sat at the other end of the towel on his knees, settled between your ankles.

“What did you assume when I asked you a number, Dean?” you asked, looking up at him.

“You were going to edge me that many times?” he asked, confusion now showing across his features. You sat up, leaning back against your hands.

“Nope,” you said, licking his lips. Dean scoffed.

“Well what is it?” he asked as you wrapped your legs around his waist, pulling yourself closer to him. He glanced down but obviously wasn’t getting what you were intending. Then again, that was the point.

“You only get that this weekend, nothing else,” you said, looking down at your lap. “No mouth, no back door, even though you’ve never asked about it. You chose three. Well that…” you said, pushing off the ground to press your core against his length. “…Is all you can have until you’re a good little boy again.”

“You’re not very good at being the dominating one, you know that?” he chuckled, even though you could feel him growing hard against you. You rolled your hips and he gasped.

“Maybe this is my not so subtle hint that I like to be nice to my Frat boy,” you said, grinding yourself against him. “I’m not good at being in charge,” you said as Dean’s hands found their way onto your back, fingers nipping at the strings of your bikini.

“Y/N?” he asked as he pressed his bare chest against your body, his hand undoing the bowtie behind your neck.

“Hmm,” you mumbled into his shoulder, slowly moving your hips over him, the friction helping him grow hard. You felt the tie fall away as Dean pulled effortlessly on the one across your back, you top falling between the two of you. He plucked it up and tossed it to the side, pressing on your hips lightly so you’d sit up for a moment. As you did, he slid off his trunks and then your bottoms, leaving both of you nude as he guided you to sit back on his lap and grind against him more.

“I trust you to do that with me you know, if it scares you,” he said, his hands running over your back. You lifted your head so you could look at him. His eyes were soft.

“I know, Dean,” you said as Dean adjusted you on his lap, letting the head of his cock rub against your clit, sending pleasure coursing through you.

“But you don’t like it,” he said, resting his head against yours as he placed a hand on your thigh, rubbing up and down. You were quiet as he rocked his hips gently, his tip hitting your clit, your pussy dripping against him as it asked for more. “It’s okay, I like taking care of you. I’m still your good little boy, even if you’re not pinning me to a bed,” he said, touching your cheek so you’d look at him. 

His eyes were sincere and you nodded against him. You were afraid of letting him know you were all talk, that you had no real desire to call the shots. Working together or letting him set the tone, that was what you truly wanted.

“Dean,” you moaned, your hand tugging on the back of his head. He knew what you wanted as he lifted himself up, pressing into you slowly. You squeezed his shoulder when he was all the way in you, this new angle letting him have perfect access to your g-spot. Dean pulled back slowly, his cock rubbing roughly against it and you dug your fingers into his skin, sure to leave bruises. He whined against you but placed a hand against your lower back. “Oh fuck,” you groaned out, the pressure forcing his tip to press into your most sensitive area.

“Y/N, how are you so fucking tight,” he grunted as you both pulled back and came together roughly, creating animalistic sounds in the other. You let your mind wander as you started to ride him more forcefully, his thrusts increasing in strength.

“Dean, Dean, Dean,” you muttered over and over again as his rhythm fell out of pace with yours, both of you trying to push the other over the edge first. The slap of your skin echoed in your ears as his hands gripped you tightly, holding you down against him as he burst inside you.

“Ah!” you both cried out at the same time, Dean’s cum shooting into you with such force your orgasm came suddenly, the pleasure of it more sharp than normal, the bliss more mind numbing. You dug into him with all the force you could, holding him tight as he bit down softly against your shoulder, his teeth grazing the skin. He rocked his hips slowly as each of you came down but didn’t pull out immediately. With your legs and arms wrapped around him, you were so close you didn’t want to let go just yet.

Dean peppered you with kisses as you began to feel the ache in your legs, the muscles tiring from being so tense. Reluctantly you let go as Dean’s hands came under your ass, lifting you up and setting you down in front of him. You leaned up to give him a kiss on the cheek, his lips busy holding a smile.

“Now what?” you asked, content with letting all that had happened be your failed attempt at punishing him. He sat back as he ran a finger across your cheek.

“Want to get cleaned up and then go fishing?” he asked. You chuckled and Dean raised his eyebrows skeptically.

“I haven’t been fishing since I was a little girl,” you said with a laugh. Dean smirked as he sat up on his knees and helped you to stand.

“It’s not that hard, you’ll remember,” he said, picking up your bathing suits and laying them out in the sun to dry, watching you walk back towards the house.

 

“What?” said Dean with a grin as you covered your mouth to hide a giggle. “You mean you don’t want to use my superhero fishing pole?” he said as he held one adult sized pole and well, something a six year old boy would use.

“I would love nothing more, Winchester,” you said as Dean handed you the old relic. He grabbed a small tackle box as he walked it down to the small dock he’d pushed you off of earlier. He cast out his line and sat down, letting the tips of his bare toes dip in the water. You walked over and tried to cast as well but you’d forgotten how.

“Straight back sweetheart,” he said as you realized you were putting too much of angle on it. You tried again and the line went out easily, landing a good distance away from Dean’s. You sat besides him, your feet not coming close to the water as Dean moved one hand off his pole, moving it behind you to prop himself up. You scooted back so he could feel you against him and found his hand move to rest itself on your hip comfortably. “Sorry about the kiddie pole,” he said after a few moments.

“It’s no problem,” you said, watching the bobber drift on the water. 

“I kind of forgot Sammy and I broke a few when we were up here before the semester started,” he said, lifting his hand to move the bottom of your elbow so you’d turn your pole, obviously seeing something you weren’t.

“You’re close with him,” you said, no question in your voice. Dean hummed next to you.

“He’s my baby brother. It’s my job to look out for him,” he said, reeling his pole in and setting it to the side. He shifted position so that he was behind you, reaching his arms around you to place his hands over yours, as he slowly started reeling in before stopping. You watched the water careful before you saw movement underneath.

“You’ve looked out for me too, Dean,” you said as you watched the bobber wobble. Dean teased the fish in before the bobber went under and his hand started working with yours to pull it in. Then it popped back up and you saw the fish swim towards you obviously no longer hooked. You sighed as you sat there, Dean resting his head on your shoulder, waiting for the next one to come along.

“Y/N, how come you called me the other night? I mean we weren’t exactly the best of friends at that point,” he said, your body tensing beneath him. “You’re my friend now, a  _really_  good friend, but then…”

“I knew you’d come if I asked. You’re a good person,” you said, resting back against him.

“Your other friends aren’t good people?” he asked, a sigh escaping you.

“Can we just sit here together and fish and cook hotdogs and have campfires this weekend, not talk about…” you trailed off. Month long deal or not, you were certain he’d run once he found out the truth about you. 

“Alright,” he said, nuzzling his cheek against yours, the hairs tickling you. “Favorite professor you’ve had so far?” said Dean, continuing his game of asking you random questions like he’d done over the past couple days.

“Professor Nick, duh,” you said with a sly smile as Dean let his hands fall from you and wrap around your waist, squeezing slightly.

“What was that?” he said, his lips brushing your earlobe.

“You’re cute when you’re jealous,” you said, turning your head to face him. He pouted before putting his hands back on top of yours.

“Or like,  _all the time_. I’m adorable,” he said, as you nodded your head against him. “Tell me I’m not the cutest thing you ever laid eyes on,” he said and you only laughed. “Told you so.”

“You are certainly something,” you said, his long legs adjusting so they moved you forward. “Don’t you dare,” you said, letting go of the pole and holding onto him for dear life.

“Don’t I dare what?” he said, pushing the two of you closer to the edge of the dock. From where he sat behind you, he could push you in no problem.

“Do that!” you said and he moved forward again, only a little bit of your thighs still on the edge.

“Do that? Okay,” he said with a laugh as he pushed you forward once more, now the only thing truly keeping you from going in was his strong arms wrapped around your waist.

“You win! Now pull me back!” you said as Dean moved the pole to the side. 

“See the problem is-” he started but you rolled over Dean’s leg to the side, scooting backwards at the same time you used your hands to shove him forward. 

“What’s the problem?” you said cockily when he broke the surface, his eyes impressed.

“No problem at all,” he said, grabbing for the dock’s edge and pulling himself up. You stood back as he climbed up, dripping from head to toe. “How about a hug for my sweetheart?” he said, opening his arms and advancing on you. You were able to make it back on the lawn when Dean wrapped his arms around you, your shirt soaking immediately. You shrieked at the coolness of his body as he lifted you off the ground. “Now what to do with you…” he trailed off, turning between the lake and house.

“I vote house,” you said eagerly. “I’ll make you a pie. You love pie,” you said, recalling how excited Dean got when you’d stopped at a diner the night before.

“Lake it is,” he said as he walked you over just to the edge as you closed your eyes, waiting for the chill of the water. Instead you felt yourself be set down on the grass. “Are you really going to make me a pie?” he asked, shedding his shirt and throwing it near your now dry suits.

“Pecan?” you asked and he rolled his eyes back like he did when you went down on him. He must have really liked pie.

“Yes please,” he said, the childishness in him turning from teasing you to wanting dessert. 

“No lake?” you asked, nodding behind you.

“I promise not to shove you in the lake again until after you’ve made pie,” he said, rocking on his heels.

“Wow, a two hour reprieve. How generous of you,” you said as you walked past him, hiding your smile. You’d never let him know you liked him teasing you as much as he liked to do it. You were almost at the back door to the house when he called out to you.

“Don’t use up all the whip cream,” he said with a wink. You rolled your eyes. “ _For the ‘smores_ , Y/N. Not everything is about sex,” he said as he walked towards you. He brushed past you inside but not without hesitating first. “Now the chocolate syrup, that is  _most definitely_  for sex,” he said leaning down over you.

“You better go buy some then Frat boy because I used up the last of it on my pancakes,” you said, crossing your arms.

“I will see you in an hour then,” he said, pressing a kiss to your cheek before running towards the front door, car keys in hand. You tossed him a hoodie off the back of the couch to cover himself up with so they’d let him in the store. “Thank you sweetheart!” he called out before running out the front door.

“That’s my Frat boy,” you said, turning with a smile, hoping to have his pie in the oven by the time he got back.


	7. Chapter 7

**Summary for the Chapter:**

> Dean and reader have a campfire one night and find out some things about each other…

When Dean Winchester said he liked pie, he was not kidding around. It had gotten to the point that you were almost jealous that a pastry was pulling sounds from him only you thought you were capable of you.

“Will you marry me and make me this pie everyday for the rest of my life?” he asked when you’d finally taken it away from him, telling him he had to make it last the weekend.

“I think you like this pie more than me, Winchester,” you said as you placed it in the fridge. Dean pouted, an actually legitimate pout, but resigned himself.

“You’re a close second, sweetheart,” he said, walking over to you. 

“You know how to make a girl feel special,” you said as Dean placed his hands on your shoulders. He put some force on them, moving you away from the fridge. “Dean…”

“I’m not getting pie,” he said, reaching inside. “I had my dessert, now you get yours,” he said, pulling out the brand new bottle of chocolate syrup. You laughed as he licked his lips.

“You’re serious?” you asked as he beckoned you to sit on the counter. You did as he took off the plastic, and squirted just a little his mouth. He hummed and closed his eyes. When he opened them again you’d already taken your shirt off.

“I wanted to take that off,” he whined. You shrugged as you let one bra strap fall from your shoulder, then the other.

“I’d hurry up or there’ll be nothing left,” you said, cocking an eyebrow as you undid your bra, exposing your chest to him. He bit his bottom lip as he watched you glide your hands down your body, stopping once you got to your shorts. You had put on your black ones from before, no button or zipper to toy him with. Instead you tucked your thumbs into your underwear, shimming it and the shorts off your hips every so slowly, Dean eagerly waiting for you.

“It’s much sexier watching you do it,” he said and with that, you lifted your ass, slipping the things down your legs and letting them fall to the floor. Dean moaned as he took you in.

“I’m waiting for my dessert, Dean,” you said, taunting him. He roved our your naked form, sitting on his counter as you slid a hand down to your breast. “If you’re not going to give it to me…” you said, taking your nipple in your hand and twisting it between your thumb and forefinger.

“Fuck, Y/N,” Dean said as he watched you start playing with both of your breasts, making the buds hard.

“I wish it was you doing this to me,” you said, looking up through your eyelashes. That was all he could handle as he took the quick step over to you, his lips crashing into yours as his hand found your breast and started kneading the flesh. 

“Move your hands, Y/N,” he said, pulling away. You did as he asked as you saw him pick up the bottle. He brought it to one of your nipples, squeezing just a drop on it. His lips came down on it and you arched your back, hands finding their way into his hair.

“Dean!” you gasped as he hungrily licked and sucked, lapping up every last ounce of chocolate. He pulled away much too soon as he let you taste the chocolate on his tongue, pouring more on your other nipple. You giggled in excitement, waiting for Dean to suck that one clean. His lips wrapped around the small bud, his tongue assaulting it with more force than the other as you moaned. “Fucking shit,” you breathed out when Dean came up.

“Lie back sweetheart and I’ll give you the main course,” he said with lust filled eyes. You swiveled your hips so you could lay against the cool counter, letting your legs hang off the edge, your pussy exposed to him. His hands ran light touches over your stomach and down your hips, the tickling sensation causing you to buck them up. “Eager?” he said, with a chuckle. You lifted your head up to watch him as he picked up the bottle. Your chest heaved as you let your head fall back against the counter once more.

You let out another gasp as you felt something cool and wet drizzle over your clit. You ran your hands in your hair as you felt Dean’s hands on your inner thighs, spreading them. His breath was hot on your core and then you were arching your back as his tongue licked over your clit.

“Holy shit,” you let out as Dean’s tongue started running over the bundle of nerves, over and through your folds, drinking down the sugary substance like you were candy to him. You thought he must have gotten it all so quickly but he just ran his mouth and tongue over you again and again, licking up every last trace of it. He took your clit in his teeth gently, his tongue running back and forth, back and forth over it as you started to whimper.

“You okay sweetheart?” he said, pulling away. You fisted your hand in his hair roughly, a small wince appearing on his face. 

“More,” you said, your voice much lower than normal, need laced in the demand.

“I was just getting more sweetheart,” he said, the cool, dripping sensation running over you again. “I wish you could taste this. Your juices with chocolate? Divine,” he said, bringing his lips to you again.

“Dean,” you moaned as he started to play a game with himself, lapping up as much syrup as he could before it traveled down you, forcing his tongue to work overtime on your clit. “So good to me,” you praised him as you ran your fingers through his hair. Dean hummed against you and you bucked your hips, some chocolate getting on the tip of his nose. He nipped and sucked until you were moaning so loud, begging him to make you cum that you couldn’t think straight. 

You screamed as he locked his lips around your clit and sucked hard, his tongue swiping over you relentlessly. Your back arched far off the counter as you rode out the bliss of your orgasm, the feeling almost too intense. Dean worked you through it before moving back, and standing upright again.

“I’d ask how that was for you but I think you enjoyed it,” he said with a smile as he stood next to you, your body trembling slightly at how hard you’d cum. He stroked a hand through your hair as you regained your bearings.

“When do I get to do that to you?” you asked, sitting upright to face him.

“Monday I suppose. I only get that wonderful little cunt this weekend if I recall,” he said.

“You’ve got something to look forward to then,” you said, reaching out and grabbing him by the shirt collar. You pulled him down and he parted his lips, expecting you to kiss him. Instead you brought your lips to the tip of his nose, sucking off the small chocolate residue that had found it’s way there. You licked your lips at the taste of his skin mixed with the syrup. “Yup, your cum and that is definitely going to taste good,” you said, eyeing him up and down.

“Can’t wait,” he said, brushing a strand of your hair behind your ear. You placed a hand on his chest.

“But I…I don’t…” you started, trying to find the best way to phrase what you wanted to say. Thankfully Dean knew what you were getting at.

“No more today. I just want to hang out and cuddle with you tonight. We can do more tomorrow if you want. Or take a break. Whatever you want is okay with me,” he said, his hands rubbing up and down your bare arms. He helped you off the counter as you went to take your third shower of the day. By the time you were done, the sun had started to set and the temperature dropping.

“Hotdogs for dinner?” you asked as you walked out into the living room in a pair of jean shorts, a hoodie and sneakers. Dean had put on a pair of sweatpants and wore his same hoodie from earlier.

“I just lit the fire,” he said as you looked out back, seeing the campfire Dean had set out in the middle of the back yard. “And set up the tent if you’re still up for that,” he said and you nodded. You grabbed a few plates and the food as you followed Dean outside.

“This is fun,” you told him as he handed you a poker to put your dinner on. He laughed as he placed one on his and you held them over the fire, the sun almost all the way down.

“That’s why I like it here so much,” he said, sitting besides you on a log he’d rolled over. You leaned your head against his shoulder without thinking but didn’t tense up like normal. “Food’s done,” he said. He ripped open a package of buns and handed you one. You’d burned yours some but it still tasted good. Before you knew it, you had another one and Dean was placing a marshmallow on your poker.

“You know how you got a good ‘smore?” he asked, taking the melted thing off the metal stick and placing it on some chocolate.

“How?” you asked as he handed you the first one. You took a bite and rolled your eyes back as you hummed.

“It makes you do that,” he said, making one for himself. You stayed like that for a while, making each other ‘smores until you both felt like you would burst. Dean collected the food and everything else you’d brought before tossing it inside, brining two blanket’s back out. He lay one out on the ground near the fire for you to sit on and placed the other one near you in case you got cold.

“You think of everything,” you said as he sat besides you, wrapping an arm around you so you’d lean into him. He rested against the log as you rested against him, no sounds except for the crackling fire and the quiet night. Looking up you saw more stars in the clear night sky than you could have ever imagined. You lay against Dean, his warmth filling you as you looked up at it, letting peace fill you too.

“Y/N,” Dean said as he brushed your cheek. You turned to look at him, his eyes shining, even in the dim light.

“Dean?” you asked. He leaned in and kissed you like so many times before but you knew this was different.

“I love you,” he whispered. Your heart stopped as you searched his face for doubt, that he was lying, that he was only telling you what you wanted to hear. You couldn’t find anything and suddenly you realized what that look was that he had sometimes, the one you couldn’t figure out. He’d been falling for you right in front of you and you’d never even realized.

“I can’t,” you whispered, your voice croaking. Fuck. It was all over now. Dean looked like he’d just been hit by a bus.

“I thought, I thought you liked me…liked me for more than just that stupid bet,” he said, pain and sadness coming through in his voice. You sat up and turned to him, his eyes starting to shimmer. 

“I want to say it. I want to say it back  _so fucking bad_ , Dean, you don’t understand,” you said, trying to plead with him.

“Then say it,” he said, still broken. You looked away, pain raising up in you.

“I can’t!”

“Why not?” he said, never raising his voice. His hand touched yours and you couldn’t fight it back anymore.

“Because then I care! And when you leave me, I can’t handle that again,” you said, wiping away the tears that had formed in your eyes. Dean’s hand wrapped around yours as you tried to shrug him off. He grasped it tight, forcing you to look at him.

“I’m not leaving you, Y/N. Why are you so afraid to care? And why won’t you talk about your friends? Why-”

“I don’t have real friends Dean. I have people I talk to, that doesn’t make them my friends,” you said, hardening your gaze. His hardened in turn but instead of him getting pissed he just looked sad.

“Why are you afraid?” he begged and you had to fight back another round of tears. 

“I’m alone, Dean. My parents are gone, my best friends are gone. My scar is from a surgery that saved my life from four years ago. One stupid fuckin’ car accident and I’m the only one left. Guess what, nobody wants the 17 year old at the foster home. No body wants the kid that’s afraid of getting close because they lost everyone they loved. That’s why I can’t say it, Dean, because I’m going to lose you because you only  _think_  you like me. People don’t want me,” you said. Dean sat in silence as the tears ran down your face. You couldn’t even see his, your vision so blurred. 

Then he was there, his lips on yours, your cheeks wetting his. He put everything he had into it, every touch, every laugh, every wonderful moment you’d spent with him. He pulled back as he brought his hands to your face, cupping your cheeks so you’d look at him.

“I love you. I don’t care if you’re too scared to say it now. I’ll spend everyday of the rest of my goddamn life trying to prove that I am hopelessly and utterly in love with you, Y/N. So you better get used to me being around because I’m never leaving you,” he said, his eyes wet. Then you stopped crying, something lifted off of you by his words. You knew he meant what he said and even if someday you lost him, well you’d let him cause you that pain because he would have been yours.

“Say it again,” you asked, reaching up a hand to wipe his cheek. 

“I love you,” he said, dropping his hands from your face and taking yours in his.

“I love you,” you said back effortlessly, a smile on your face as he glowed.

“I love you,” he said with a laugh and you couldn’t keep from laughing with him.

“I love you,” you said as he pulled you against him. Now you understood all those tenses of his body, the sighs, the ghost touches. He wanted to be yours just as badly as you wanted to be his. You stayed in a tight embrace for a long time and when you let go, you weren’t afraid anymore that it would your last time. Dean sat back against the log and you took up your position from before, only now pulling the blanket over your legs. Dean pressed his lips to your forehead and your heart fluttered.

“That was less painful than I feared,” he chuckled. You lay a hand across his chest.

“You were expecting worse?” you asked him.

“I thought you might say you didn’t feel the same. That would have been horribly devastating,” he said. You snuggled into his chest. He cared. You weren’t just a bet to him. You were his sweetheart and he was your…

“Do you like being called Frat boy? I can call you something else,” you said as Dean stroked the top of your head.

“I like it because you made it up for me, even if I never was a very good Frat boy,” he said sheepishly.

“What do you mean?” you asked as Dean avoided your gaze. You remembered earlier in the day when you were swimming and Dean said he could be himself at the house, not have to act like something else. “Dean…”

“Promise you won’t laugh at me,” he said, his cheeks flushing pink in the dark. You nodded.

“I won’t laugh,” you said as Dean let out a sigh.

“The night we met, the first time we…”

“Yeah?” you asked. Dean’s brow creased as he rubbed his hand across his face.

“That was my…first time ever…like…you’re the only person…I’ve ever been with,” he said, avoiding your face. You punched him in the chest as he let out an oomph. 

“Dammit Dean! Why didn’t you tell me! I would have made it special!” you said, wishing you’d been soft and kind to him for his first time, rather than asking him to be rough with you.

“I’m 21, Y/N! In a frat! I was all talk! And you were beautiful and I didn’t stand a chance if I didn’t put on my cocky asshole act…and it was special because it was with you,” he said. 

“No more secrets between us, got it?” you said and he nodded. You were quiet again as the both of you watched the flickering flames. “Well, you’re above and beyond the best I’ve ever been with,” you said.

“You’ll always be my best,” he said. “Never going to touch anyone else besides my girlfriend,” he said, trying the word out for the first time.

“Would my boyfriend like to go on a romantic star lit walk?” you asked, lips pulled up into a never ending smile.

“Your boyfriend would like that very much,” he said, shifting so you both sat upright. As you stood, Dean reached over behind the log to grab a camping lantern. You waited as he lit the oil inside and it filled with light. As you walked closer to the dirt path that ran around part of the lake, it gave off enough light so that you wouldn’t be tripping but let you stay in the dark some.

“Dean,” you said as he reached down his hand and interlaced your fingers. He started walking one way down the path, the lantern in his other hand.

“Mhm?” he hummed happily.

“I shouldn’t have been afraid to tell you earlier,” you said, wrapping your free arm around his bicep, holding him close as you began to wander farther from the house.

“No, you shouldn’t have. I guess you’d tell me something similar that I shouldn’t have been embarrassed?” he asked. You nodded against him. “Anything else we should get out of the way?”

“I have something else kind of big you should know about,” you said, Dean tensing under you.

“What it is?” he asked gently. You sighed.

“I don’t really like pie,” you said, putting as much feigned sorrow as you could into your words. Dean let go of you and clutched his heart dramatically.

“How can I ever look past such an atrocity?” he asked, spinning around. “This can’t be happening!” he scoffed. He wrapped his arm around your waist, as your bodies shook with small laughs. “I think I can live with this horrible indiscretion as long as you continue to make me pie for the rest of my life. I think that’s an even trade,” he said.

“Rest of your life?” you asked as Dean’s grip on you tighethened.

“What part of never leaving you don’t you understand sweetheart? You and your pies are never escaping me,” he said. You leaned your head against his shoulder as you walked down towards where the lake began to curve.

“Escaping? I suppose if I had to be held against my will by someone I’d pick you,” you sighed, wrapping your hand around his waist.

“Thank you victim, I mean sweetheart,” he said, kissing the top of your head. You stayed in silence for the next thirty minutes or so as you walked for a while before turning around and heading back, the stars reflecting off the calm surface of the lake.

“What’s this going to change?” you asked Dean as you stepped off the path to see the fire had almost dwindled out.

“No more bet I suppose. I’m sure the guy’s will have field day with this but-”

“You think so?” you said, placing a hand on your hip. Dean only raised an eyebrow.

“Well not with you around to protect me,” he said with a smile. Dean blew out the lantern as you climbed in the tent. You both kicked off your shoes and your pants. 

“One sleeping bag?” you said with a chuckle as you pulled off your hoodie, leaving you in a tank top.

“It’s a double,” he said, patting the spot besides him. You sat down as Dean shed his warm outwear, revealing nothing beneath. You couldn’t keep yourself from taking him in. “It’s going to get hot in here, easier to do it now than when you’re sleeping on me.”

“I’m not complaining,” you said grinning. Dean crawled in on the right and leaned down to pull the zipper up. “Dean,” you said as he rounded the corner at the bottom and you suddenly felt the bag get much snugger. “Dean…” you said again as Dean leaned over you to bring the zipper up. “Oh my…” you said, putting a hand on your face as Dean pulled the zipper all the way up. “Double sleeping bag my ass,” you said, turning to face him. You could feel him close to you, very close to you, not that you wanted him to be anywhere else. This was maybe a little much for sleeping though.

“It’s always been enough room for just me,” he said as he moved his arm to find your waist. 

“Dean, I’m smaller than you but I’m not that small,” you said, reaching to undo the zipper. Dean pouted as you opened the tent flap. “I’ll be right back,” you said as you took off towards the house. When you got inside it was dark aside from the one light you’d left on. You walked over to where you believed a closet was and opened it. It took you a second but soon you found what you were looking for and were heading back outside.

“What are you doing?” you heard a voice in the tent say as you came back in. You tossed in another sleeping bag the same size as Dean’s and rolled it out. Only you spread them out fully, undoing the zippers so that you could zip the two seperate bags together. “You’re a genius,” said Dean as he realized you’d made a much more comfortable bag for you both to sleep in.

“Save the pillow talk for the morning,” you said with a wink as you crawled in next to him. “That’s an invitation in case you-”

“Do I RSVP with you or…?” he trailed off as he threw his body over yours. “Hey, Y/N,” he whispered.

“Yeah?” you asked.

“Look up,” he said, turning your cheek so you were on your back. He’d left the tent’s roof cover off, letting you see the night sky.

“Wow,” you whispered, leaning into him as you gazed upwards. “Always think of everything,” you said to him, snuggling into his chest.

“Goodnight, Y/N,” he said quietly, a smile in his voice.

“Good night, Dean,” you said, a smile in yours.


	8. Chapter 8

**Summary for the Chapter:**

> Dean and reader finish up their weekend getaway…

You woke to the sound of deep breathing, Dean sleeping peacefully besides you. From where your head lay on his outstretched arm, you knew he let you use him as a pillow last night. His other hand was on his rising and falling chest, perfectly relaxed. Under the cover of your sleeping bag you could tell he’d twisted his lower half, wrapping your legs between his long, muscular ones. 

He was peaceful, his skin soft, lips pink in the morning light. He had freckles on his nose, on his cheeks. They were little light ones, but they were there. He always had a defined face but you’d started to notice how it smoothed after he was rested. Maybe he was stressed. Well you’d both been stressing a lot recently…but hopefully that was done with.

His eyes moved under his eyelids for a moment before stilling. You figured he’d wake up soon, honestly you were surprised to find yourself up before him, your body still exhausted from the day before. They flickered again and you sighed gently. His lips parted and you took in his short stubble. You always thought stubble would be scratchy to you, unpleasant. Dean’s was somehow smoother, the little prickles ticklish on your skin. 

His hair was skewed about, the strands stuck up at funny angles that defied gravity. You smiled as you took in his bed head, took in how cute he looked as you remembered you’d get to wake up next him from now on, get to look at all those things over and over again.

“Y/N,” he mumbled groggily as he suddenly woke up, blinking a few times before his eyes caught yours. He gave a shy smile as he lay next to you. “Good morning, sweetheart,” he said. 

“Morning,” you said back as he rubbed the sleep from his eyes. He stretched the one arm he could that wasn’t currently under your head before gently resting it across your waist. “No trapping me this morning?” you asked, aware of how he normally reacted to waking up besides you.

“Already got you,” he said, letting his body be still. “But since you love it so much…” he said, quickly rolling so he lay on top of you. “You’re comfy,” he said as he rested his chin on yours.

“You’re hilarious,” you said, tilting your chin, moving his as well so your lips met. 

“You taste like chocolate,” he said, rolling to the side and sitting up.

“You taste like you ate four hot dogs,” you said cockily, bringing yourself up to sit. Without being under the cover, you instantly felt the cool morning air on your arms, tucking them around yourself to get warm.

“But they were  _good_  hot dogs,” he said as he crawled around the back of you. “Here,” he said, his hands tugging at yours so he could move them up in the air. After a moment, you felt something soft and warm be pulled over your head, your hands be pushed through sleeves. It was too big to be your hoodie though as Dean pushed the hood that covered nearly your whole face back, revealing him sitting in front of you with a sleepy smile.

“You realize this is mine now, like you’re never getting it back,” you said, unable to keep from nuzzling into the cozy material, somehow much better than your own sweatshirt. This one smelled like him.

“Then I get yours,” he said, crawling to the other end of the tent and digging through the corner to find it at the bottom of your clothes. He picked it up and raised an eyebrow. You rolled your eyes as you watched Dean struggle to try and fit into it. If it had been a zip up…maybe he could have done it. But currently he had his head stuck and couldn’t get the thing over his shoulders. “How do I look?” he asked, swinging around to face your general direction.

“Sexy, Frat Boy. I’m getting wet just looking at you,” you said, unable to hide your laugh. Dean gave a thumbs up before retreating out of it before he stretched it out further than he already had.

“Well at least that statement’s true for one of us,” he said. You smirked as he scoffed. “Y/N, you in my shirts, now my hoodie?” he said, placing a hand on his chest. “No, nope, such a turn off. I mean,  _hello_  we both know I was referring to  _me_ ,” he said, biting his lip as he finished so he wouldn’t turn up his lips. You nodded your head as you crawled over to him and straddled his lap.

“That’s not what little Dean says,” you said, glancing down to see Dean’s morning wood through his boxers. He glanced down at himself and a small blush appeared on his cheeks.

“Despite what  _that_ …is doing, I thought I might give you a break today if you want?” he asked hesitantly.

“A whole day of no sex with Dean Winchester? How ever will I survive,” you said, placing your hands on your cheeks. 

“I don’t know really, such a pity for you,” he said, brushing his lips against yours. 

“Maybe…tonight…if we’re…in the mood,” you said, Dean nodding his forehead against yours.

“Like I said yesterday, whatever you want is always okay with me,” he said gently, his hands rubbing up and down your arms caressingly. 

You were going to respond but you couldn’t for the life of you find the words. He was…good. He could be cocky as hell and a huge tease but at his core, he was a good man. You couldn’t begin to tell him how it felt to be able to have him want you.

“Y/N, you haven’t…changed your-” said Dean before you pinched him. “Ow!”

“Don’t ask stupid questions, Frat Boy,” you said, moving off of his lap, opening the tent flap to step outside. Your feet were covered in morning dew the moment they touched the grass. You turned around to face him and leaned in, ruffling his hair. “You’re mine Dean Winchester. I’m not going anywhere,” you said before finally reaching your hand back. Dean sat there, his hair beyond messy with a content expression, like the one he’d had when sleeping.

“Like I’d let you leave,” he scoffed. You chuckled and headed towards the house.

“Breakfast time lover boy,” you said, waving for him to follow you. He crawled out on hands and knees before standing and stretching, his muscles rippling in the morning light. He gave you a sly grin as he caught you staring at his chest again.

“ _Y/N…_ ” he sang as he walked over to you. You looked away, feeling the blush rise up in your cheeks. You could see Dean’s feet come into view and his hands were on your wrists, bringing your hands up against his chest. Slowly he moved them, letting your hands explore his body. “You’re adorable when you blush. I should make you do it more often,” he said as you felt him up and down, a small twinge running straight to your core.

“I’m not going to last until tonight if you keep trying to turn me on,” you said, Dean chuckling at your words.

“Sorry if I make you so horny, Y/N. Some of us have that thing called self-control,” he said, leaning down to kiss your forehead.

“Why don’t you go take your self-control into the bathroom and take care of that thing while I make us something to eat,” you said, glancing down at his erection. “Unless…” 

“God you love sucking my cock, don’t you little girl?” he said, his eyes flickering dark for a moment. You promised you wouldn’t suck him that weekend, but that didn’t mean you wouldn’t help him along in his time of need. You took him by the wrist now, using one of your hands to tug down his boxers so his erection sprang free as the other moved his hand to wrap around himself, slowly moving his hand so he’d work himself over until he understood what you were doing. 

You let go and stood behind him, wrapping your arms around his chest, running them up and down like before. His arm jerked slightly as he worked himself over. You wanted to watch but knew you’d get too worked up if you did. You wanted to be fresh for him that night. You rested your head against his bare, muscled back as you dropped your voice to something you knew would drive him wild.

“I do love sucking it, Dean. I love having that thick long cock in my mouth, have my lips wrapped around that massive thing. It feels so good. I love it when you fist your hand in my hair and feed it to me, fuck my face hard, when you shove that huge fucking cock down my throat, Dean. I love when I take you all, make you cry out those moans, when you swell and throb and twitch. I love all of that, Dean. I love it so much. But you know what I love the most?” you said, making your voice breathy for him as he pumped over his length faster and faster. He was making those sweet little moans you loved and you knew he’d cum soon.

“What,” he whined as you let your hands dip down and run circles over his hip bones.

“I love when you cum, Dean. I love when you cum down my throat, shoot stream after stream of your hot cum inside of me. It fills me up, it tastes so good. Salty and sexy and it’s all you, baby. It’s all you, Dean. When it fills my mouth, when you fill my tight cunt, it’s amazing Dean. When it dribbles out of me, I can feel it run out so slow it’s heaven, you let me taste you after you’ve fucked my pussy. It tastes like both of us, but you, you taste so much better. It’s so strong and wonderful on my tongue, I’d drink your cum down everyday if I could Dean. I love it so much, I love when I can make that cock of yours cum,” you said as Dean moaned out, his body going tense beneath you. Glancing around him you saw him cum, the force of it strong as he pushed himself through his orgasm.

“Fuck,” he said, panting beneath you as he relaxed. You smiled against him and patted his chest.

“How’s little Dean doing now?” you said as you unwrapped yourself from him. Walking in front of Dean, his face was glowing, his brain trying to remember how to speak.

“I’ve never made myself cum that hard…like ever,” he said, his pupils still wide as he stepped out of his boxers and picked them up. He walked past you as you grinned wide, glad you could help him.

“Aw, look at your cute little butt,” you said, taking in his backside properly for the first time. Dean’s hand instantly tried to cover it with his boxers.

“That’s sexy cute little butt to you,” he said, holding up a finger. You laughed as you walked inside and patted him on the back.

“Breakfast will be ready by the time you’ve cleaned yourself up,” you said, parting from him to walk into the kitchen. He smiled as he gave you a wink before heading towards the bathroom.

 

After you’d filled yourselves with pancakes, eggs and bacon so much that it felt as though you’d burst, Dean advised you of what you should wear that day and told you to meet him by the dock. You slipped into your bathing suit and a pair of bright red running shorts. You decided to forgo the tank top. He’d teased you plenty with the way he’d licked the syrup off his plate earlier. The least you could do was return the favor.

As you walked outside with sunglasses on, a bottle of water and the tank top in your hand, _just_  in case, Dean let out a long whistle. 

“Like what you see?” you said, twirling around for him with a smirk. Dean laughed as he beckoned you over.

“Your bathing suit’s on inside out sweetheart,” he said. You looked down at your chest. 

“No it’s-” you got out before Dean’s hands were on you, swinging your legs around his waist as he pulled you into a piggyback.

“Such a tease,” he said, walking off towards the right to an area you hadn’t explored yet. You were quiet as you looked at the lake, noticing how private it really was. Then Dean was setting you down much too soon and taking your things from your hands.

“Kayaks?” you asked as you noticed the two boats that had been dragged down from a nearby supply shed. Dean put your things in the red boat that had Sam’s name carved in the side. 

“It’s not hard,” he said, taking you by the elbow and picking up a paddle. “You just do this,” he said, holding the stick out in front of you and holding his hands over yours, moving the paddle up and down, side to side.

“I think I’ll get the hang of it,” you said as Dean dragged his bright yellow one down into the water.

“If you need help, just beg me and I’m sure we can work out some sort of arrangement for my services,” he said with a wink, moving to pull yours down. You crossed your arms and popped out your hip, following him down into the water. It covered your feet and felt nice and cool between your toes.

“Favorite color’s still blue right?” he said, walking back towards the shed. You smiled and saw Dean run back out with two bright blue lifejackets. He slipped his arms through the holes of the larger one as he brought a very similar, just smaller looking one over to you.

“Thanks for the child size, Dean, but I’m not that small,” you said as Dean rolled his eyes. He placed your hands through the holes and zipped you up, buckling the few straps across your chest and torso before tugging on them to secure them.

“I used this one before I hit my growth spurt,” he said, placing his hands inside the straps that ran over your shoulders and giving them a good tug, pulling you forward into him.

“You must really not want me to drown, huh,” you joked as Dean held on to you tight.

“Well, then I have to dive in and rescue you and save your life and then you’re forever indebted to me and you fall madly, deeply in love with me and it becomes a whole thing,” he said, waving his hand in the air. You giggled against him and shook your head. “Aw, she’s blushing again,” he said as you pulled back.

“In your dreams Winchester,” you said, ducking your head down and moving your hands to secure his lifejacket for him.

“Shall we continue this on the water?” he asked when you were done. You ran over to your kayak eagerly, waiting for him to push you in. “Well what are we waiting for then?” he said with a smile.

 

“Are you sure you want to head home?” asked Dean nervously. You rolled your eyes for the fifth time as you placed your bag by the front door. 

“Dean if we head home tonight, we’ll get home around midnight and don’t have to worry about rushing back for class Monday,” you said, trying to help him remember that it was his idea in the first place.

“Are you-”

“Yes, now stop worrying that I don’t like you anymore because I do,” you said, his body relaxing. 

“Alright, let’s head out then,” he said, picking up your things as you looked around the cabin one last time. You were sure you’d be back there again soon.

 

“We probably should have checked the weather,” said Dean as he stared at his phone in the dark. You were pulled over on the side of the road. You’d gotten fairly close to home, much faster than you thought you would because no one was on the road. Apparently those people all saw the torrential storms that were supposed to come through. 

“Yup,” you said, leaning against him as you sat in Baby, the rain coming down so hard you could barely hear Dean. Dean ran his fingers up and down your arm as you both waited, hoping for a break in the weather. The longer you waited though, the storms got worse and the later it got. Soon you found yourself growing tired.

“Do you want to lay in the back? It’s more comfortable for you,” said Dean, his hands playing in your hair. 

“I want to stay next to you,” you said, feeling Dean’s head come down to rest against yours. He shifted and you sat up, watching him swing his body over the front bench and sit on the back seat. He took off his boots and threw them in the footwell. He opened and closed his hands as you followed his cue, taking off your sneakers before climbing back to lay next to him. Dean leaned down and grabbed a blanket he had in the back with one hand, pulling it over yourselves as you settled in.

“Warm enough?” he asked, rubbing his hands up and down your arms again. You snuggled into his hoodie that you were wearing, absentmindedly placing a hand on his lap. He inhaled sharply as you smirked before looking up at him. You didn’t say anything as you slowly started to palm him through his jeans. Dean opened his mouth to speak but you put more pressure on him, puling a moan from his lips.

“What was that?” you asked. Dean’s eyes fluttered as you put more pressure on his growing erection, Dean whimpering something sinful at your touch. “Something you want, Frat Boy?” you asked, undoing his belt and tossing it on the floor. Dean was content to lie there and let you get him off again but you saw something shift in his lustful eyes.

“I want-” he said, the hand in your hair squeezing it for only a second before both of your hands were on him, tugging his pants and boxers down. You didn’t give him any time to prepare as you wrapped your lips around his semi-hard cock, barely any precum there for you lap up from his slit. He bucked up as you went down on him fast, moving your tongue roughly against his underside, opening the back of your throat to take him down easily.

You moaned around him as he bucked again. He put his hand on top of your head but he didn’t need to hold on, you were going down on him harder than he thought possible, your hands pinning his hips to the seat below. He withered beneath you but you kept on him, feeling his tip hit your throat with every mouthful of him. You felt him swell up, knowing he would cum soon. With one quick movement you pulled off of him and squeezed him tightly at his base, denying him his orgasm.

“Y/N,” he groaned, his hands reaching for you, trying to touch you anywhere and everywhere. 

“Shh, little boy,” you said, leaning back so you could pull off your own shorts and underwear. Dean’s eyes were shut, still so close to his release. You waited until he’d backed away from the edge before straddling his lap and lowering yourself down on him.

“Dean,” you moaned as he stretched your walls, every little twitch of him pulsing straight through your pussy. You rose up so you could come back down on him but Dean had other ideas, his cock slamming up into you, a whelp escaping you.

“Want me to cum in that tight cunt?” he asked roughly, his hands finally finding their way to your hips, pulling you down so he could thrust in as hard as he wanted. 

“Yes,” you begged, letting yourself fall onto his chest, Dean’s pumps into you becoming faster, his length dragging along your walls.

“You want it hard?” he said, his fingers digging into your skin. You grabbed onto his shoulders and dug in just as hard.

“I thought you’d have figured that out by the way I was sucking you off,” you said, one of Dean’s hands sliding down to squeeze your ass. You smiled darkly and he caught it.

“Dirty little girl, she wants it in the ass doesn’t she?” he growled in your ear. You nodded against him. Fuck, how was this the same man that made you feel so safe and comfortable. He could be so kind and gentle and then… “I asked you a question, sweetheart,” he said, his one hand kneading the flesh of one of your cheeks as he pounded into you.

“Someday, but-”

“Not tonight, that’s okay. Anything…” he said as he thrust up with more force than before. “For…” he said again, your walls gripping him like a vice. “My…” he said, his cock quivering as your heart raced, knowing you were about to feel that glorious pleasure of him erupting inside of you. “…Sweetheart,” he said, pressing in deep, hitting you farther than he’d done before, your own release hitting you before his.

“Fuck Dean!” you cried out as your pussy constricted around him, his tip bulging before spraying cum deep inside you. Dean groaned louder than you’d ever heard as you rocked you hips, prolonging the orgasm for both of you. After a minute, you rolled off of him and sat next to him, pulling the blanket on top of you. Dean huffed besides you as he closed his eyes, completely spent.

“I love you,” he whispered between breaths, tucking you into his chest.

“I love you too, Dean,” you said, falling asleep in the back of Baby with him, thinking how glad you were to know he was yours.


	9. Chapter 9

**Summary for the Chapter:**

> Dean and reader return home and transition into the next part of their relationship…

Dean and you woke up around four in the morning, the storms having passed you by finally. In an hour you were back on campus, the two of you stumbling into your apartment and crawling into your bed.

“Y/N,” Dean said as he lay on your mattress. You chuckled. “You never put the sheets back on the bed, did you?” he said as he ran his hand over the cotton of the bed beneath him. You sat up to go pull them out of the washer, certainly dry after days of sitting in there. “No, it’s fine,” he said, softly pushing you back down as he spotted your favorite blanket on a chair and covered you in it. 

“You need something,” you said, knowing the blanket was too small to cover both of you. Add in that your heat hadn’t been on in a few days and it was the end of October, you knew he’d get cold easily. “Stay here,” you said, groggily walking out to your living room and pulling the one Dean liked off the back of the couch.

“Thank you,” he said when you handed it to him. You were asleep before he could even drape it over himself.

 

“Hi, Y/N,” said Sam when he saw you waiting in the foyer of the frat house on Monday night. “You look nice,” he said. You smiled, looking down at your black dress. It wasn’t like Dean hadn’t seen you in it before. But then again, he hadn’t seen you in it when you were together.

“Dean! Your girlfriend’s here!” yelled Gabe as he spotted you as he came down the stairs. He gave you a friendly grin as he walked over to you and Sam. “So you two getting pretty serious huh?” he asked. You saw a few heads whip around from the nearby couch in the front room, obviously listening in.

“Um…” you trailed off, not sure how much Dean wanted them to know.

“Gabe,” said Dean as you saw him come down the stairs in a suit. He eyed Gabe dangerously before giving the other young men the same look, letting them know exactly how serious he was when it came to you.

“So Y/N, when ya moving in?” joked Cas from the safety of the couch. A few of the others snickered as Dean wrapped an arm around your waist. 

“I don’t know Cas. We might have to soundproof our room first,” you said, placing a hand on Dean’s chest. “Dean can get me a little rowdy sometimes,” you said with a wink. You watched their eyes move from your face to Dean’s, a few jaws slightly dropped.

“As you can see, feel free to be yourselves around Y/N. She’s just as dirty as the rest of you barbarians,” he said as he looked down at you sweetly. “Want to go on our date now?” he said, his green eyes excited.

“I would like very much to go on our date,” you said, Dean smiling and turning you towards the door. “Don’t wait up boys,” you called out, Dean stifling a laugh besides you.

“Let’s get out of here before they start plotting how to steal you away from me,” he said, opening the door.

“I wouldn’t worry about that Frat Boy,” you said, walking onto the porch, Dean right on your heels.

 

“Did you enjoy dinner?” asked Dean as he lay besides you on your bed. You snuggled against him. 

“Very much so. You were a perfect gentleman,” you said, looking at the clock knowing he had to go soon.

“Can I take you out again tomorrow?” he asked, looking at you.

“Yes. As long as I can make you dinner Wednesday,” you said, rubbing your hand in his hair. 

“Sounds good to me,” he said before letting out a big sigh. It was late and you both had early classes the next day. “I should have brought my backpack…and some clothes,” he said, not moving away just yet.

“We’ll figure out a schedule, Dean,” you said, knowing he didn’t want to leave as much as you didn’t want him to. But unless you were living together, sleeping next to each other every night wasn’t going to be feasible until you worked out the kinks.

“I’ll see you at lunch tomorrow,” he said, pulling you into a hug and giving you a slow kiss goodbye.

“Goodnight Dean,” you said, as he pulled away and stood up sadly.

“Night sweetheart, see you tomorrow,” he said, walking out of your room. You listened to him as he walked out and locked up your front door, having given him your spare key earlier that evening.

You changed into one of his shirts you had “accidentally” packed in your bag and threw on a pair of shorts, crawling into bed, the space seeming too big for just you now. You just hoped you’d figure out how to make this work soon.

 

By Thursday you and Dean had set up a plan and it was working pretty well. He had clothes at your place, you had some at his. You would both do your best to make sure you brought your backpacks with you on school nights, not caring so much on the weekend. It was Friday though and you were going to a Halloween party at a different frat that night so it didn’t matter where you ended up really.

“Hey, Y/N, should I get this?” said Dean as he held up a sexy nurse costume at the party store. 

“We don’t want to scar people for life Dean,” you said as you poked around at your options. You and Dean had gone with Sam, Cas and Crowley. They were actually looking for a costume while you and Dean had decided not to dress up.

“Wait, Y/N, this is the one,” said Dean holding up a sexy cheerleader outfit. You rolled your eyes.

“Why don’t you try and find a sexy lumberjack? Oh wait,” you said, throwing him a smile as you pointed at him in his flannel shirt. He pulled his lips up.

“Sexy school girl? Oh wait,” he said, mimicking you as he stared you down. You placed a hand on your hip and saw Dean do the same.

“Man child,” you muttered. Dean raised his eyebrows before throwing his arms over your shoulders.

“Your man child, sweetheart,” he said, lowering his head to kiss you.

“Guys, save it for the bedroom,” said Crowley as he walked by wearing a cowboy hat.

“Alright, Sheriff,” said Dean, Sam snickering as he walked up to the group. 

“Sure you guy’s don’t want costumes?” said Sam, holding up something that looked very much like a couple’s outfit.

“We’re good Sammy. Dean and I are done playing pretend with each other,” you said, looking up at the blonde man. He smiled, knowing perfectly well what you meant as Sam just shrugged you off.

“I think we’re ready to go so if you two are done,” said Cas, holding his choice in his hand.

“Whatever you say, doctor sexy,” said Dean chuckling as you walked past.

 

You’d lost track of Dean at the party probably fifteen minutes earlier when he bumped into some friends and you’d bumped into some people you knew. None of them would shut up about how hot Dean was. Eventually you were able to break free from them when you excused yourself to use the bathroom. 

“Can you hold this?” you said to one of Dean’s frat brothers, handing him your drink as you walked inside. After a minute, you came back out and he handed it back to you. “Thanks,” you said, taking a long swig, downing the whole thing.

“No problem,” he said, turning away. You thought that was a little rude but he was probably drunk and he had held it for you so you didn’t let it bother you.

But ten minutes later you didn’t feel right. You felt drunk. You’d been drinking but you knew no way in hell should you have been like that. Your mind was slipping.

“You need some fresh air?” asked Dean’s frat brother as he saw you obviously having a hard time.

“Yeah, thanks,” you said as he helped you outside. He led you down the front steps and down the street until you were alone next to a car. Maybe he would drive you home if you asked.

“Not with any friends tonight?” he said, brushing up against you. You laughed.

“I’m here with Dean silly, and his frat brothers. That’s you,” you said, wiggling a finger in his face. Why were you doing that? He smiled darkly.

“Right, of course,” he said. “He uh, wants me to take you home,” said the guy, his body trapping you against the car.

“Okay,” you said, a hazy fog hovering over you. “Let me just tell Dean I’m going home,” you said, pulling out your phone. The guy grabbed your wrist and took the phone from you.

“I already told him, no worries,” he said, grinning again. You nodded. “Now let’s-”

“Get the fuck away from her,” you heard Dean say. He sounded mad. You were sure he was just going to tell you goodnight before you went home.

“She’s drunk dude, I’m just helping her get home,” said the guy, backing away from you. Dean looked at you and you saw his face shift from pissed to…you didn’t know what it was but it wasn’t good.

“You drugged her?” said Dean, his fists shaking. One of them pulled you back behind him, holding onto you so hard it hurt. Dean snatched your phone out of the guy’s hand and shoved it in his pocket. “You  _drugged_  my fucking girlfriend?” said Dean, pulling his fist back so fast you felt the air shift as he connected it with the guy’s face.

The guy knew he had no chance as he scrambled back and was running for it. Dean wanted to go after him and beat him to a pulp but knew you were in no shape to be left alone, evidenced by the fact you had fallen on the ground.

“Ow,” you said, rubbing the palm of your hand. Dean lifted you up, his body trembling.

“Guys, what’s going on?” asked Sam as he ran outside, having heard his brother yelling. Dean breathed deeply as you wrapped your arms around him, nuzzling against him. 

“I’m taking Y/N back to the house. Someone tried to hurt her,” said Dean, the vein in his neck throbbing. He must have been really angry but you thought he was still nice and cuddly despite that. “We’re going home, Y/N,” he said, unwrapping you from him and holding your arm to help steady you.

“Night night Sammy!” you called out as Dean walked the two of you back to the frat house.

 

“Ow,” you said, putting both hands to your head. You hardly ever got hungover and never blackout drunk. How much did you have to drink?

“Here,” said a cold voice as a glass of water and a few pain relievers were placed on the beside table. You sat up and greedily took them both when you realized Dean wasn’t in bed with you, he was sitting in his chair he’d pulled over, still wearing last night’s clothes. He looked pissed.

“What happened?” you asked, a small tremor to your voice. He’d never looked at you like that before. He softened his gaze but his face was rigid.

“Did you take a drink somebody gave you?” he asked and you shook your head.

“No Dean, I’m not stupid. I gave it to Tom to watch for me for like five seconds,” you said, still unable to remember a thing. Dean sighed heavily before running his hands over his face.

“That wasn’t Tom, Y/N. It was some asshole who looked like Tom and some asshole who drugged you. You were this close to getting in a car with him when I found you. The worst part was you didn’t even realize how much danger you were in. You know what he would have done to you if I hadn’t shown up?” said Dean, his voice loud. You took in his words with a blank expression as you curled your knees up, wrapping your arms around yourself. “You have to be more careful, Y/N,” said Dean as your mind started to process what he was saying.

You didn’t notice it yourself but Dean’s expression soon changed when he saw you shaking on the bed. You knew you were still a little wide eyed, your face a bit frozen. He was right, you were so stupid. 

“Sweetheart, say something,” said Dean shaking you gently. You gazed down to the floor, avoiding him. He was probably still mad. “You’re scaring me,” he said, his hand under your chin, bringing your eyes up to meet his.

“I’m gonna go,” you said, trying to make your voice steady. “I’m just gonna grab my stuff-” 

“Where the hell do you think you’re going?” said Dean, wrapping his hands around your arms, keeping you in place. You looked around at anything but him.

“I told you before, Dean. Caring means you can get hurt and look at how upset you are. The sooner we call this off, the less it’s going to hurt you,” you said. “I don’t want you to get hurt because of me.”

“I am sorry I yelled but I would gladly be scared to death everyday over something happening to you than give you up. I’m not leaving you,” he said, his voice calm. He was so sweet and you were the screw up. He deserved better. “Stop that, please,” he said, his voice pleading.

“Stop what,” you said. 

“I love you, Y/N and I’m not letting you out of my sight until you know the reason I’m pissed is not because I’m mad at you. It’s because I’m supposed to stop stuff like that from happening in the first place,” he said quietly.

“You did stop it,” you said, letting your arms fall from your legs.

“Barely,” Dean scoffed.

“I’m sorry I’m like this,” you said, running your hands over your face, Dean’s hands on you more gentle now. “I really hate it when you look scared like that,” you said. Dean gave you a smile.

“Take a number,” he said. You moved your arms to drape over his neck, pulling him down close. 

“I love you. I’ll be more careful from now on,” you said to him, running your fingers in the back of his hair. 

“Promise me something,” he said against you, his hands on your back, rubbing up and down.

“Anything,” you said.

“The next time you try and break up with me, it better be because you hate me with every fiber of your being and you don’t love me anymore. Even then I’m not letting you go without a fight,” he said, stilling against you.

“I promise,” you said quietly, letting him hold you. You stayed like that for a long time as he relaxed. “Let me love you,” you whispered in his ear.

“As long as I can love you back,” he said, lowering you back on the bed.

You were both soft and slow, the physical need for intimacy not there as much as your mental one, the desire you both had to come together, make one another feel safe again. When you were both content, sure the other wouldn’t run off, you watched Dean drift off to sleep, his mind finally able to rest knowing you were okay.


	10. Chapter 10

**Summary for the Chapter:**

> Dean and reader attend a football game where they remember some untried things from their weekend away…

When your eyes fluttered open you saw it was close to noon, Dean’s hand around your waist like you expected. You intertwined your fingers in his, feeling his slow breathing on the back of your neck speed up.

“Morning,” he whispered, nuzzling himself against you. You smiled as he cuddled you, his grip on you a little stronger than normal as he most likely remembered the night before. “How you feeling sweetheart?” he asked.

“I got you. I’m perfect,” you said, squeezing his hand gently, his grip on you easing. “Game’s in a few hours,” you said as Dean let go of you to stretch.

“You’ve never been to a game with the guys,” he said with a chuckle. “Sure you want to hang out with a bunch of rowdy frat boys?” You laughed before rolling out of bed, still wearing nothing from that morning’s excursion. Dean’s eyes trailed up and down you only for a moment before finding your face again.

“I like one Frat Boy in particular. His friends are pretty nice too and we skipped out on them last weekend,” you said, walking into Dean’s bathroom. He hummed in agreement.

“You know they’re going to be riled up if we win, probably throw a party,” said Dean as you heard him stand up from the bed. You ducked your head out the open door to spot him throwing a black tee on. 

“A party at the frat house? On a Saturday? That’s never happened before!” you mocked as Dean tossed you some of your clothes from his bottom drawer he’d given to you.

“Laugh it up. I have plans for you tonight, sweetheart,” he said with a dark smile. You smirked.

“Do you now?” you said, crossing your arms and leaning against the door frame. He chuckled.

“If you want a whole party full of people hear you scream my name when I make you cum, I guess that’s your decision,” he said, crossing his arms in response. He raised his eyebrows and stared you down. 

“Maybe I want a whole party full of people to hear my good little boy scream  _my_  name,” you said, walking over to him, cocking your head. He dropped his arms and his face turned darker still.

“ _I said I have plans tonight, little girl_ ,” he said, bending down to get at your eye level. He gave you a cocky grin as you squinted at him, knowing he was doing it to bring to your attention how much bigger he was than you. “If you behave for me, maybe I’ll let you do what you want to me,” he said, standing upright and staring down. Then it hit you exactly what he was doing.

“You fucker,” you said with a laugh as Dean shrugged with a smile. “You’re still using the bet to do what you want, aren’t you?”

“Hey, I love you sweetheart, bet or no bet and I’m gonna love you for the rest of my life,” he said, sweetness returning to his voice for that brief moment so you’d know that was the real him talking. “But don’t make bets you can’t keep little girl. According to my count, I’ve still got two whole weeks left unless…”

“Unless what?” you said, not backing down but not failing to notice how he was turning you on with the idea of brining your bet back into your sex life. He brushed a strand of hair behind your ear before you found his hand fisted ever so gently in the back of your head.

“Unless you’re too scared to realize I was holding back,” he said darkly, his hand running soothing circles in the back of your hair. You let out a whimper without telling your body to do so. Fuck he had you good.

“Two weeks, still yours. Then I’m going to figure out some way to win one of these damn bets and own you for the next  _year_ ,” you said, Dean’s hand falling away. He pressed a hand to his heart and smiled.

“Aw, my sweetheart wants me calling the shots for a whole year,” he said, as you scoffed.

“I’ll win a bet one of these days,” you said and saw Dean’s eyes flash with a thought but not saying it just yet.

“So tonight?” he said with raised eyebrows. You patted him on the chest.

“All your’s Frat Boy, whatever you want to do this body,” you said, grabbing him by the wrists so you could run his hands down your torso. “But if we lose today, I get to do whatever I want to  _that_  body tonight,” you said, dropping his hands and pointing at him. 

“That’s not fair. We’re so unbelievably the underdog it’s painful,” he said, crossing his arms and pouting. 

“Too scared?” you said, mimicking him from before. He scoffed. 

“Deal,” he said, holding out a hand. You smiled as you headed in the bathroom to get ready for the game. For once you were going to beat Dean Winchester at one of these bets.

 

“Hi, Y/N,” said Dean with a shit-eating grin as he waited for you outside of the bathroom. You grumbled at him as he grabbed you from behind and pressed his head against yours. “I love you,” he said, more happy than he had any right to be.

“Love you too,” you mumbled as his chest rumbled from laughter. He let go of you as you walked over to the concession stand, Dean grabbing a beer for each of you and a snack.

“You have really shitty luck, you know that?” he said after he paid. You rolled your eyes as he was handed your items and you headed back towards your seats. “I mean, who could predicted that theirquarterback _, back up quarterback, three running backs, and half of their defensive line_  would have all come down with the stomach flu last night. Those poor little freshman out there really didn’t stand a chance against our guys,” said Dean, cockiness radiating off of him. 

You climbed the few steps back into the stadium to see the scoreboard. Any other day, you wanted your team to win but it seemed as though you were meant to lose every bet you ever made to Dean. The board showed a seven score lead, something the other team would never recover from. Dean let you slide into your row first, trying to walk through the bleachers unscathed. You turned back to him when you found a small gap and silently held out your hand, asking for his drink.

He handed it over with a long stretch of his arm. About ten seconds later when he was stumbling by the two men even taller than him, he gave you a thankful smile. You handed it back to him when he reached you as you both carefully made your way over to your spot beside Cas.

“What took you guys so long?” joked Gabe from the row in front of you. “Bang one out in the bathroom?” he said. Dean held out his beer over Gabe’s head.

“What was that?” joked Dean, pulling it back before he accidentally did knock it on him. “Girl’s line is horrible,” he said.

“Better get used to it Dean,” said Cas as he nudged your arm. “Y/N has to put up with everything awful about you after all.”

“I could tell her stuff about him that would send her running for the hills,” said Sam, leaning down between you and Cas. You laughed as Dean turned to face his little brother.

“Too bad, Y/N was going to introduce you to that Ruby girl she tutors,” said Dean with an evil smile. Sam shook his head at his brother but looked at you with pleading eyes.

“The one in 18th century American? Cute with dark hair?” he asked sweetly, that certain Winchester kindness behind it. You rolled your eyes.

“Ask her out, Sam. Girl’s like a Winchester that takes charge,” you said, Dean’s free hand wrapping around your shoulders.

“Speaking of that…” he whispered in your ear.

“Party tonight at the house if you two love birds are interested,” said Gabe. You scoffed.

“The other team could turn it around,” you said and instantly found about ten heads whip around, even those not really listening to your conversation.

“Are you rooting for the other team?” asked Chuck as the others watched you curiously. You were instantly shaking your head as Dean chuckled.

“Y/N’s just being pessimistic, aren’t you sweetheart?” he said, his hand giving you a squeeze. You nodded and let them turn their attention off of you before Dean was whispering in your ear again. “Sure you want to spend the night at my place, might get a little loud,” he said, his breath hot and sticky on your skin.

“Lot of big talk, let’s see if you can deliver,” you whispered back, looking up at him through your lashes when you pulled away. He gave you a smile and nodded as the third quarter began.

“Game on,” he said, paying attention to nothing but you.

 

“Dean!” you giggled as he carried you up to his room on his back, his laughter filling the space.

“Watching you turn down guys is so much fun for me. Especially when you tell them I’m your boyfriend,” he said, reaching the third floor, his floor. 

“Those poor boys downstairs couldn’t handle me,” you said, hearing the distant beat of music from down below. Dean was quick to unlock his door and bring the two of you in the dark room, closing it behind him. He flicked on a small light before setting you down on the bed.

“No, I don’t think they could, sweetheart,” he said with a cocky grin. He crossed his arms as you sat up on your knees and crawled to the end of the bed, watching him from the other side of the room.

“You gonna do something big boy?” you taunted. “Or just stand there and look pretty?” you said, licking your lips. He smirked as he walked to his small refrigerator. You were confused for only a moment before he was tossing you something. A bottle of chocolate syrup.

“I was doing some thinking,” he said. “It appears that you, my dirty little girl, owe me not one, but  _two_  things you promised to me last weekend,” he said, standing in front of you. You smiled as you swung your legs off the bed and left the bottle, standing so that you could dip your hands just so into his jeans.

“I know I made one,” you said, nodding to the syrup and how you’d promised to suck him off. “But the other?” you asked and Dean tsked you.

“She doesn’t remember,” he said, your fingers working on undoing his belt. You pulled the leather from the belt loops and tossed it aside. “Maybe I’ll play with myself tonight little girl until you do,” he said as his hands found your wrists. You whined and tried to look at him as innocent as possibly.

“I want to touch you,” you said, Dean’s hands still on you but not stopping you from pulling down his zipper. You placed a hand on either of his hips and easily slid the jeans down, leaving him in only his shirt and boxers. It was a sight you saw every night when you went to bed and every morning when you woke up. But right now it was the sexiest thing on earth to you.

“You going to do what I ask?” he said as you hooked your thumbs in the elastic of his underwear. You nodded as you bit your lip, Dean’s hands releasing you. Your hands went up instead of down as you slid them along the sides of his torso, puling his shirt off of him so you could see his strong abdomen. He smiled and gave you a quick but harsh kiss. “You want me naked?”

“If you’d like me to return the favor, all you have to do is say,” you said. Dean’s hands practically clawed at you, shedding your shirt and pants, getting you out of your bra and underwear by the time you’d found your way back to his boxers and tugged them down. When the two of you stood in a heap of clothes, Dean kicked them to the side.

“I want it rough and hard,” he growled in your ear as you shuddered. The two of you had been so sweet as of late, you’d almost forgotten how primal he could be. 

“Aw, good little boy is asking me to be tough with him,” you said with a lustful smile, splaying a hand on his chest. His hand was on you quickly and gripped you tight.

“Oh, I wasn’t asking. I was telling you how it’s going to be,” he said, a quiver of want running through you. One look at his face and you were on your knees in front of him before he could even laugh. You reached for his hips but stepped back, keeping you at arms reach. “You haven’t remembered yet,” he said, placing a hand gingerly on his growing length.

“How am I supposed to remember?” you groaned. Dean took a step back, close enough for you to touch your lips to him if you leaned up but you knew he’d never let you. Instead he’d tease you. You could see the precum leaking from him as he wiped it away from his tip and used his thumb to smear it around his hard shaft. 

“Listen to what I’m saying, dirty little girl,” he said and you fought back the urge to roll your eyes. He wasn’t saying anything he hadn’t said before. “ _My dirty little girl_ ,” he said slowly, suddenly making it painfully obvious to you.

“I remember…Daddy,” you said, raising yourself up on your knees, Dean dropping his hand from himself. He smiled as he ran a hand against your head. You could feel yourself dripping down your thighs as Dean shook his head. “Daddy?” you asked when Dean’s arm caught your elbow and lifted you up. He tossed you back on the bed as he climbed next to you, twisting himself so he was laying on top of you.

“You can cum whenever you want tonight, sweetheart. But you only get to do it once, understand?” he said, twisting his head around so he could see your face. 

“Let me suck your cock already,” you said. Dean raised an eyebrow as he hovered over you. You leaned up and sucked his tip into your mouth greedily. Suddenly you felt Dean moan as he brought his lips to your clit and you bucked up slightly, taking more of Dean in your mouth than you planned.

You’d never 69′d before and you knew Dean hadn’t either. But damn if you two hadn’t gotten into a perfect rhythm quick, you didn’t know what to call it. He thrust shallowly into your mouth, your cheeks hollowing around him as he switched between assaulting your pussy with his tongue or ravishing your clit with rough swipes. You knew you were close but he was closer, his cock throbbing every time you made the smallest movement against him. 

You felt Dean breathe sharply through his nose as he came, his cum spilling down your throat as you swallowed around him. When he came down, he pulled himself from you but kept going on you, determined to send you over the edge. You didn’t want to cum though, not yet.

“Ow!” he said, pulling away, reaching a hand to his ass where you’d lightly pinched his cheek.

“Whoops,” you said with a devious smile. “You were trying to make me cum,” you said as he sat up, your juices covering his face as you saw him notice the dribble of cum that adorned yours. You sat up and brought your lips to his, each of you chasing the taste of yourself on the other. You expected the kiss to be short but Dean wasn’t backing off, making sure you were far away from an orgasm before breaking from you.

“You didn’t use the chocolate,” he said, kicking if off the bed. You shrugged.

“Next time,” you said, watching his hand find your breast and softly play with the bud.

“I want to try something, Y/N,” he said quietly. You gave him a reassuring smile.

“I trust you,” you said. He laid you back on the bed, leaving your breasts to dip a lone finger in your soaked cunt. It tried to grip onto him but it wanted something more. Dean teased you, getting his finger drenched before pulling out. “O-Okay,” you stuttered out when you felt him move down, touching the dripping finger to the tight ring of muscles around your ass.

“Only a finger tonight, nothing more,” he said. You reached a hand down to his hair and tugged on it, a small wince crossing his face.

“Go ahead, Daddy. We’ll work up to the bigger stuff some other night,” you said, feeling him nod beneath you. Even though one of his fingers was not that big, you’d never had anything up there. He went slow, your muscles tensing around him as he came to an eventual stop.

“Feel good?” he asked. You moaned and he pulled it back out slow, a gasp escaping your lips. Dean watched you carefully as you got used to the movement and saw you start trying to thrust down onto him. “Want Daddy’s cock in that pussy?” he said low. You tugged on his hair again, pulling a gasp from him that time.

He eyed you mischievously as he thrust his cock in hard, giving you barely any time to adjust to him as he pulled out again. You moaned as he lifted your hips, giving him a deeper angle to pound into you with, all the while keeping his finger in your ass. It was such a small thing but both sensations at once was definitely something you were enjoying.

“Dean,” you moaned as he placed a hand on your hip. He ran slow circles against the bone as he bit his bottom lip.

“Louder,” he said, slowing his thrusts. You groaned louder.

“Dean,” you said, loud enough for you to be heard by someone in the empty room next door. He slowed his thrusts even more, despite his end being close.

“Louder sweetheart,” he demanded. 

“Fuck, Dean,” you said, louder still. He came to a complete stop in you as you grunted loud enough for the floor below to hear. “Dean!” you yelled and he started to pumping in you again, rewarding you with harder thrusts the louder you got.

“So good for me,” he said, his finger moving in tandem with his cock, the feeling sending you close to the edge. He wasn’t even encouraging you to make noise anymore, you  _wanted_  to make noise, let everyone know how good he made you feel.

With one quick pump in you, you came undone, your body clenching his cock and finger, gripping them as his free hand found your clit and rubbed carefully there. You bucked up on him, screaming as a second, even more powerful orgasm hit you hard.

“Fuck, Dean!” you yelled as you remembered how to breathe. You felt your body resist as Dean pulled his finger from you first and then his cock. You would have been perfectly content to lie there letting them fill you. Your head swam as Dean rolled off the bed and washed up, coming back with a washcloth as he cleaned you up.

“You guys okay in there?” you heard Sam say through the shut door. Dean smiled as he knew he’d gotten the party downstairs to hear you.

“More than okay, Sammy,” you called out and heard him laugh. 

“You better tell her dude before I do,” said Sam as he walked away. You propped yourself up on your elbows.

“Dean…” you said as he looked at you sweetly.

“I was never really going to let a whole party full of people hear you like that. You just hold back a little when we’re at the house. Sammy turned up the music as soon as we came up. Nobody heard you but me, promise,” he said. You fell back on the bed, an amused smile on your lips.

“Daddy’s devious, isn’t he?” you joked as you heard Dean shuffle around. He lifted you up as he pulled back the covers, setting you down and climbing in beside you.

“You got turned on by that though, didn’t you?” he asked as he tucked you against him, once again your cuddly frat boy. 

“That’s not the only thing,” you said. “Maybe next time we’ll try something a bit…bigger?” you asked. Dean hummed.

“Two fingers?” he joked as he slapped his chest lightly. “We’ll work up to it,” he said, pressing his lips to your forehead.

“You really are too sweet to be a frat boy,” you said, looking into his bright green eyes. You saw them crinkle as he smiled.

“But I’m your Frat Boy,” he said, his eyes fluttering with sleepiness. You gave him a small smile back as you yawned.

“All mine,” you said. You closed your eyes for only a moment and opened them to find Dean asleep, his chest rising and falling softly. “G’night Dean,” you said, snuggling closer and shutting your eyes.


	11. Chapter 11

**Summary for the Chapter:**

> Dean and reader reach the last night of their month long bet. However Dean has an idea for another one…

“You’re smiley today,” you said, walking into the frat house to see Dean lounging on the couch. He was absolutely beaming, his face in a smile all day long from the moment he woke up, walked you to class and had lunch with you. He was in such a good mood, his eyes watching you like you were heaven on earth to him so often that day, you’d almost forgotten what tonight was.

“He’s head over heels in love with you in case you haven’t noticed,” said Sam from the other end of the couch. 

“I’ve noticed,” you said, rocking on your heels as you blushed. Dean’s eyes lit up when he saw your cheeks flush, crinkles in the corners from where he was smiling so hard.

“We’ll see you in the morning Sammy,” said Dean, rolling off the couch. He walked over to where you stood by the door, watching as he shrugged his coat on over his body in the cold nighttime, November air. He looked cute even in all those layers.

“Don’t drive off to the cabin without me tomorrow,” said Sam, looking at you more than Dean. “Y/N?”

“We won’t forget about you Sammy,” you said with a smile. “You never forget about the cute Winchester,” you said, glancing up a Dean with a smirk. You heard Sam laugh as Dean crossed his arms and nodded his head.

“I must be the hot Winchester then,” he said, a smile still on his face as he held out his hand for you to hold. “See you in the morning, Sam,” said Dean, not looking back as the two of you headed out the door.

It was evening and the sun had set a long time ago. But you never once felt scared with Dean by your side, not like you used to. Dean kicked a small pile of leaves on the sidewalk, a skip in his step as you giggled.

“How did we end up here?” you said aloud to yourself. Dean gave your hand a light squeeze as he found more leaves to disturb as you walked.

“Must have been fate,” said Dean, nothing in his voice to indicate he was joking. You wrapped your free arm around the one that held your hand, dropping your head against him as you walked. “I really love you, you know.”

“I love you too, Dean, in ways even you’ll never be able to understand,” you said, letting that familiar sense of calm fill you that settled over the two of you on your walks. “Thank you for inviting me to your cabin for Thanksgiving break.”

“I recall telling you that you were coming to Thanksgiving with the Winchesters, not asking,” he said playfully. You grinned against him before that small rush of fear you’d been pushing away rose to the surface.

“It’s been a few years since I’ve been to one, a big family gathering, holidays,” you said, knowing Dean could sense your trepidations.

“I’m here for you, so is Sam. By this time next year, you won’t even remember why you were scared,” he said, your body relaxing at the promise of another year with him.

“Next year?” you asked, looking up at him with bright eyes. His smile was still there and you thought his cheeks must be hurting by now from doing it all day.

“Next year, the year after that, the rest of eternity, ya know, forever,” he said. “We’re gonna have to find Sammy a girl at some point,” said Dean, his voice light and happy.

“Already planning the family reunions?” you chided him. He opened his mouth to speak but shut it.

“Planning some things….eventually,” he said, bumping his shoulder against yours playfully. “If you get what I’m saying,” he said, his eyes staring into yours. You blushed again.

“No, not at all,” you said slyly, Dean laughing next to you.

“I guess you’ll just have to wait and find out someday,” he said with a wink. The rest of your walk was in a content silence, Dean playing with the leaves when he came across them, you getting lost in the way the wet road reflected the moonlight so well.

“Home sweet home,” you said when you turned the corner to head up to your door. You didn’t move your arms from Dean as he turned the key, letting you both inside. Reluctantly you let go of him, flipping on the light switch as Dean took off his boots and coat, locking up for the night behind him. You kicked off your boots and pulled your jacket off, watching as Dean left you and headed straight for your bedroom. “Well someone’s ready to get down to business,” you said, following him.

“I got loving to do woman, get in here,” he said with a laugh as you stopped in your doorframe.

“What are you doing?” you said, shaking your head at him. He smiled.

“Nothing,” he said, his hands behind his back. “I wanted to…discuss the terms of our bet,” he said. You raised an eyebrow.

“Tonight would have been our last night together if you hadn’t turned out to be the Frat Boy of my dreams,” you said, a light shade of pink running across his cheeks.

“Nor you the sweetheart of mine,” he said, the both of you staring at the person who’d chosen you. “But I’d like to make a new bet, one that lasts a whole year,” he said, his eyes a little dark.

“I always lose to you,” you pouted but Dean only shook his head.

“Trust me, you want to lose this time,” he said. “You in?”

“Stakes?” you asked but Dean gave you look that said he wasn’t telling. “Yes, I’m in you cheater,” you said, walking into the room.

“Good. Now would you like to know what bet you just lost?” he asked with a smirk. You squinted at him until it dawned on you. “I bet I could get you to agree to a bet without knowing what it was because you trust me. I won,” he said nonchalantly.

“You are a god amongst men. Now what exactly did I just sign myself up for?” you asked, reaching your hands out to run over his torso, feeling him react under your touch.

“One year from today, I’m going to ask you something,” he said, keeping his hands behind his back as you slid your hands under his shirt feeling the skin ripple beneath you.

“The answer’s going to be yes dumbass,” you said, looking up at him with a smile. 

“I hope so. But if I don’t make a rule right now, I might rush this and ruin it,” he said, your hands slipping his shirt over his head but getting it caught on his arms that he held behind him.

“You can’t ruin it. But we’ll play by your rules as long as you play by mine,” you said, taking in how ridiculous he looked.

“And what are those?” he asked, leaning down, his eyes shifting so you knew he was already ahead of you.

“I’d like you out of that shirt, for starters,” you said, Dean’s hands falling to his sides as you were finally able to lift it off of him. “How about those pants next…” you trailed off, Dean obediently following your words so he stood in front of you in nothing but his boxers. 

“Miss I don’t like to take charge, I think I’m rubbing off on you,” he said as you stalked around him.

“I just like you naked, you’re too handsome to be covered up by those clothes,” you said, turning on your heels before heading out the room.

“Where are you going?” he laughed as you walked into your kitchen. You shrugged.

“Oh, I was just teasing you. I didn’t actually have anything planned,” you said, giving him a wink. He half groaned and growled at your admission.

“How about you take off your shirt and pants and we’ll get this party started?” he asked.

“How about you make me?” you said, backing up towards your front door. “That is…” you said, undoing the door behind your back, placing a hand on the handle, “If you can catch me,” you said, opening the door and stepping outside, hopping down the few steps so you stood in your front yard.

“Oh you are gonna get it,” said Dean, voice smooth and low from the doorway. 

“Come on, I left you in your boxers, you shouldn’t be scared to come out here and get me little boy,” you said, egging him on. He looked like he was debating it as you sighed. You spun around, looking across the street, no one in sight. “No one is even around-Hey!” you yelled as you felt a pair of strong arms lift you off the ground.

“Mine,” was all Dean said as he carried you back inside like you were nothing. He kicked the door shut, not putting you down as he locked it back up. “I think I should get you out of  _all_  those clothes if we’re being fair,” he said, carrying you into your room. He set you down gently on the bed before he tore away at you, removing every shred of fabric on your body before you knew what hit you. “Much better,” he said, standing back and admiring his work.

“You got something planned for tonight good little boy?” you asked, sitting up and blinking your long lashes at him. He couldn’t help but chuckle as he raised his eyebrows.

“Something like that,” he said, hooking his hands in the elastic of his boxers and pulling them down, revealing his semi-hard cock that was red and leaking precum. You licked your lips before glancing up. He held up a finger and beckoned you over, a smile spreading across your face. “You are…” he began to say, placing his palm flat against your cheek, his finger tips dancing in your hair, “…the most amazing person I’ve ever met,” he said softly, lowering his head to brush his lips against your ear.

You fluttered your eyes closed, feeling his heat radiate off of him as his hand trailed it’s way down your face and neck to slip behind your back. He just breathed in hot bursts against you, something building in him that was making you wet at the mere thought.

“Do you want me to try it tonight?” he said, his voice smooth as silk but gruff, lips nipping at the skin of your neck. “Do you want me to give you what you want?” he said, the hand on your back pulling you close as his other graced over the soft skin of your ass.

“Yes,” you breathed out, feeling the short hairs on the top of his head against you, nodding in agreement. “Fuck yes. You’ve been teasing for weeks,” you whispered, placing both hands on his hips.

“Wanted you to be sure…and I like when you’re whiney for me,” he said with a devilish smile. You dipped your hands lower, letting them trace his hip bones, so different than the soft curve of yours but something about the solidity and rigidness in them that turned you on.

“You’ll be whining first,” you promised, shifting yourself off the bed so you could get on the floor and kneel in front of him. Dean prepared himself for you to go down on him fast and hard like he knew you liked to but you’d promised he was going to whine after all.

He was completely hard now, his tip engorged as the salty mixture of precum leaked from his slit. You sat up, giving your lips a good long swipe with your tongue, keeping eye contact with Dean as you did so. He let out a small whimper and you smiled. He was in for a treat tonight.

You leaned in like you were about to take his tip in your mouth but moved down to his base instead, pressing the lightest of kisses against his shaft, slowly, so slow it had to be torture for him, so slow you only made it halfway down before his hand was in your hair, fisting in tight.

“Y/N,” he growled. You only smirked as you kept at it, the squeezes of his fingers in your hair doing nothing but spurring you to keep going. You kissed close to his tip, close enough that he could get a taste of that feeling he was craving, but you only gave the one. You moved your head back towards his base, ready to lick a long line against him but his hand held you back. “Please,” he whined, so needy you weren’t sure you’d ever heard him like that before.

You obliged by guiding his hand so you could move back to his tip, let your tongue lap at it like a kitten drinking it’s milk. You closed your eyes as you relished in his taste. So salty and sweaty and so very much the essence of Dean. Sucking slowly, you slid back down his length, swallowing as his tip hit your throat, letting yourself take more of him as your lips locked around his base, your nose brushed up against his strong stomach.

“Oh fuck yes,” he said as your hands held his hips, your mouth working him despite you remaining still. “Wanna…wanna…” he breathed out, his hand twisting in your hair almost sharply. You let your hands fall away as you pulled back, leaving a long line against him, feeling the pulse of his thick vein through your tongue. With one little look and a tap of the hand on your head, he knew you wanted him to use you as he pleased.

Despite being wound up, Dean didn’t slam you down on him quickly but found a still slow rhythm. You hummed around him as your mouth begin to feel the effects of being stretched for so long, something you’d gladly go through for him. It was a low little sound that you brought up through your throat, sending vibrations straight through his throbbing cock.

Dean’s head was tipped back in pleasure as he let himself really start to enjoy it, let himself begin fucking your face with vigor.

“Finger yourself,” he said roughly, bringing his head forward so he could see your stretched lips around his member. “Make yourself cum while I cum down your throat,” he said with authority.

He didn’t have to ask twice before your fingers were running through your bare folds, running circles over your clit before dipping three fingers in yourself. You moaned as your pussy had something to clench onto, your fingers feeling the tense muscles of your own body wanting a release more than you’d realized.

Your pumped into yourself fast and hard, causing you to work harder on Dean as he couldn’t hold back any longer.

“Y/N, fucking hell. So fucking good,” he groaned, his cum shooting in your mouth, that taste you loved so much filling you up. Greedily you drank him down, giving his sensitive cock one good long suck to wipe him clean before you pulled off with a pop.

“You like that?” you said with a cock of your head, a smile over your sore lips. Dean smiled darkly as he took in a deep breath.

“You didn’t cum when I did,” he said, letting you know there was a promised threat in there. “Now you gotta work for it,” he said with a raise of his eyebrows and lick of his lips. You weren’t quite sure what he meant as he offered a hand to help you stand, guiding you with him as he sat on the edge of the bed.

Dean pulled you down for a dirty kiss, tasting himself on you, shifting your body so you straddled his thigh. After a moment he pulled away and caught his breath again, green eyes completely blown wide with love and lust.

“Ride my leg,” he growled, his hands on your hips moving you ever so slightly so you could feel your clit rub against his strong thigh below. His hands left as you brought yours up to his shoulders, giving you something to brace yourself on as you moved your hips back and forth, grinding down on him. After a few short repetitions of the motion, you could feel yourself building again.

As you felt that rise of pressure within you, it occurred to you that this was Dean’s payback for being so tortuously slow before, a delicious payback you were loving. Your wet slick covered his thigh and dripped down his leg, you body covered in sweat as you fought to keep up, go faster despite the shake of your legs.

“Dean, baby,” you whined as you started to get close. Your head rested against his, your sweat intermingled with his. He offered you praises and profanities as you rode him harder, knowing that when you finally came, it was going to be big. A hand in your hair tugged on it gently, your back arching at the touch and providing you a deeper angle to grind him.

“Come on, you can do it sweetheart. Wanna feel you cum,” he whispered in your ear, almost inaudible over sound of skin slapping against skin. Your heart was beating fast, your head was lost pleasure as each slide on him could send you over. “Please sweetheart, do it for me, Y/N,” he said low.

You let out a primal grunt as you made one long and fast glide across his leg, feeling the start of your orgasm, your mind going blank from the intensity of it. But it lasted, it lasted and lasted as you kept pushing your self, Dean’s hands find your lower back to help push and pull as your trembling legs took the pleasure that was almost too much. You could hear the blood running through you as your body tensed, the orgasm lasting and lasting until you thought you would explode.

When it finally came down and stopped, you were wrecked. Dean’s hands caught you against him and pulled you back to lie on the bed. Thinking was beyond you. All you had was your body’s desperate need to do absolutely nothing as it tried to remember how to breath again.

“Wow,” you heard Dean say after a moment, his arms pulling you up so you could lay on your bed. You opened your eyes to find him beside you, under a blanket. Shifting your legs it felt like you were under the same one. 

“I can’t do anymore right now, I’m sorry,” you whispered, Dean’s hand patting the top of your head. “You had plans for tonight.”

“My only plan was to make you feel good. I think we can safely say mission accomplished,” he said with a chuckle. You shut your eyes but kept a smile on your face, the effort of staring into his wonderful green eyes, looking at the little freckles you adored too much.

“I love you, Dean Winchester,” you said, reaching blindly with a hand for his. Thankfully he found yours and pulled you against his chest.

“I love you, Y/N Y/L/N,” said Dean, a perfect stillness to his voice. “Sleep now sweetheart. I’ll make sure we wake up on time to grab Sammy and head out to the cabin. You just sleep now,” he said, your body already lulling itself away as you could feel his relaxed heart beat.

“Night Dean,” you mumbled, drifting off before he could say the words back.

 

Five in the morning came far too soon and for once, you were the one trapping Dean in bed.

“Y/N, you realize it doesn’t work as well when you try to hold me down,” he said, tossing the covers back as your arms and legs wrapped around his torso.

“Why not?” you grumbled as you felt Dean sit upright and then actually get out of bed, your body nearly sliding off as a pair of strong hands came under your still bare ass.

“Because you’re smaller than me I can do whatever I want to you. But I appreciate your efforts of taking the lead on cuddling this morning,” he said, walking the two of you out your door and towards your kitchen.

“I can do whatever I want to you,” you mumbled back as you nibbled at Dean’s ear. He laughed as he set you down in one of your kitchen chairs.

“I’m positive you could sweetheart but I think it’s more likely you’d be standing up for me than to me. Your very protective of your Frat Boy like that,” he said, moving to your cupboard and pulling out a few bowls to make you a quick breakfast.

“Mine,” you said with a yawn, still not awake yet as Dean sat a bowl of cereal in front of you. You ate quickly, waking you up some but Dean could tell you were still a little out of it after he’d gotten the two of you cleaned up in the shower.

“Y/N, we’re driving in the car, it doesn’t matter how your hair looks,” he said, pressing a hand on your back and bending you over. You couldn’t help but notice the small shock that ran to your core as he grabbed your hair in that position. You could feel him playing with it and pulling the hair tie off your wrist and onto his. “There ya go, perfectly hot messy bun,” he said, bending you back upright as you saw he’d actually done a pretty good job.

“Want to dress me too?” you joked and saw Dean’s eyes flicker with want for a second. Dean shrugged and you thought what the hell, leading him into your bedroom so he could look at your closet.

“Whatever I pick you have to wear all day…until I decide to take it off of course,” he said with a cock of his head. You opened your arms wide.

“Do your worst,” you said, knowing he could really pick something truly ridiculous if he wanted to. But when you saw what he was picking out, you nearly aww’d. A pair of wool socks because your feet always got cold and then your favorite pair of black sweats that he loved possibly more than you since they had that magical effect of being loose on you but still showing off your legs. A light gray tee that you used for lounging around because it was so soft and comfy, often the matching top to the sweatpants and your dark gray zip up with the soft fleece. 

Then he made his way over to your dresser and you could only imagine how turned on he was at the thought of picking out your lingere. You expected him to pick a pushup bra and thong, not that you didn’t have at least one set of those packed away for the trip, but he didn’t go for that option. Instead, he found a gray bra, your “comfy” one you called it, and a pair of simple black bikini underwear with just a little lace on the waistband. 

“How’d I do?” he asked when he handed everything to you. You smiled hard as you couldn’t keep the blush off your face. He wanted you to be as comfortable as possible for the long car ride.

“Pretty good for a Frat Boy. Might have to make it up to you later,” you said as you got dressed. Dean smirked as he threw on jeans and a t-shirt, a flannel shirt over that. You made sure everything was off in the apartment as Dean checked that you had all your bags by the front door for your trip to the cabin for Thanksgiving break.

You slipped on a pair of boots while Dean did the same, pulling on his jacket as you climbed into yours. You slid your backpack on as Dean took your duffle, letting you head out first before he locked up after you. It was still dark out in the early morning, everything quiet as you waited for him to come to your side, his hand sliding over yours as you began the walk back to the frat house where Dean’s car and Sam waited.

You were yawing as you walked, the night before leaving you more tired than normal as Dean encouraged you to lean against him. He felt you giggle against him as he found leaves to play in again, the cold air offset by the warmth he gave off.

After ten minutes you were walking up the drive way, spotting Dean’s car as he tossed your bags in the trunk beside his own. 

“Want to run in and use the bathroom quick? I’m sure Sam is waiting in the front room for us,” said Dean as he checked his watch.

“I just want you right now in that backseat,” you said with a wink. Dean titled his head skeptically. “I mean what if your mom puts us in seperate rooms? Last chance for more than a week,” you said, twirling your hips. That was all Dean needed to hear as the thought of not touching you for a week sent him over the edge. His hand grabbed your wrist, pulling you into the back of Baby and lying you on the seat, his body hovering over yours.

“How do you want it?” he growled in your ear before sitting up and shedding his jacket and shirt, tossing them in the front seat, leaving his torso bare. 

“Let’s not make Sammy wait too long,” you said, Dean’s hands already tugging your sweats and underwear down to where they caught on your boots. Dean’s lips crashed onto yours, rough so they would rev you both up fast. Dean didn’t bother to undress you as he slipped his barely hard cock into you. You gasped, it felt so strange to have him limp inside you.

“You like when I fuck you in the back of my car?” he grunted, his thrusts quick as he came to life inside you. You gripped the back of his head, squeezing his hair as you felt him stretch you in a way you’d never experienced before.

“Fuck yeah Dean,” you said, bringing his head down, having discovered a while ago he liked the little hair pulls more than he was willing to admit. He moaned into your mouth as he went fast, god he went fast, his thumb running circles over your clit as he pumped into you hard, rocking Baby with the force of it. Any passerby’s would be able to tell what was going on and if that didn’t turn you as much as Dean’s cock itself, you didn’t know what did.

“Fuck, you take my cock so good,” said Dean, his voice a few octaves lower. You were practically cutting off his air as you held him to you, forcing your kiss to last as long as him fucking you was going to. You didn’t know if it was the ferocity with which Dean pounded into you or the fact that you were in the back of his car but suddenly you were cumming, gripping Dean’s cock as he thrust in hard, lodging himself deep within you as you felt him cum.

“That was a good idea,” you said as you released his hair, patting it down and soothing where you’d held on. Dean nodded as he pulled up your pants, then his own. He threw his shirt and jacket back on and the two of you crawled out the back on shaky legs. That’s when it hit you, he hadn’t screwed you in the way he’d promised to earlier that night. “I thought you were supposed to-”

“Took you long enough to remember I didn’t give that ass the loving attention it deserves,” he said with a dark smile. “Maybe I’ll make that your Christmas present,” he said low, sending a shiver down through you. “I will give it to you, but when we don’t have to rush sweetheart. For now let’s get cleaned up and grab Sammy,” said Dean. You nodded in agreement, knowing just how much he loved to tease you but that he’d give you what you wanted someday soon. You guided one another in the house to find a sleepy Sam on the couch. Dean pointed that you’d both be right back as you headed up to Dean’s room, cleaning yourselves up in his bathroom before heading back down.

“Ready?” asked Sam with a yawn. You nodded as you spotted a stray stand of hair that stuck up on the back of Dean’s head. You licked your thumb and wetted it down, Sam chuckling. “Mom’s going to get a kick out of you two,” said Sam as he grabbed his bags and headed outside.

“Why’s that Sammy?” asked Dean, running ahead so he could open Baby’s trunk and Sam could toss his bags in. It was then that you noticed the steam on the inside of Baby’s windows. Dean saw it too as he tossed you a blanket and you quickly scrambled inside to wipe her down as Dean distracted Sam for a minute. When you came back out and slammed the trunk shut, Dean knew it was safe.

“Beacuse you two are all like, in love. It’s sickeningly adorably and if you ever break up with her, I’ll kick your ass to make sure you get her back,” said Sam.

“As if you could,” said Dean, standing up straighter in front of his little brother. 

“Boys, I ain’t going nowhere and Sam, stop picking on your brother. We all know I’d kick his ass if that ever happened,” you said with a smile. Dean and Sam shared a silent conversation that seemed to agree with that statement.

“Come on, let’s get going. We promised mom we’d be there for lunch,” said Dean, walking over to the driver’s side. Both you and Sam went to the passenger side but stopped when you both saw you were going for shotgun. “Aw, now that’s adorable. Both of you looking at me to tell you who’s sitting in front,” said Dean, only a whole lot of smugness in his voice.

You and Sam seemed to glare at each other. You two had gotten to be really good friends over the past month and you were fairly certain Sam was starting to think of you as a little sister, even if you were older than him. But shotgun riding, all bet’s were off.

“Sorry, Y/N. Front’s kind of his thing,” said Dean, with an apologetic smile. You gave him a reassuring one back.

“It’s fine, Dean. I got to let you two have your brother time after all. Plus I could use the nap,” you said climbing in the back. When you were all in and Dean had started Baby you heard him mumble.

“Now I wonder why that is,” he said, turning his head so you could catch his gaze. 

“Wake me up when get to a rest stop,” you said, putting up your hood and leaning against the window, excited to being spending the holidays with some people you cared about again. 


	12. Chapter 12

**Summary for the Chapter:**

> Reader spends Thanksgiving with the Winchesters and has some fun getting to know the family…

“Up and at ‘em sweetheart!” you heard Dean yell suddenly, your head jerking away from the window you’d been sleeping against. Blinking furiously, you caught Sam laughing as he stepped out of the car while Dean turned around to see you. “Come on sleepy head, rest stop,” he said as you begrudgingly opened the back door and stepped out into the cool morning air. You yawned as you stretched, Dean’s hand finding yours as you stood on your tip toes and he gave you a small tug forward.

“Are we there yet?” you asked as Dean and you followed Sam into the rest stop. Thankfully it wasn’t as crowded as you’d anticipated, Thanksgiving still a ways away and you mostly saw other college students heading home for break.

“Another few hours and we should get there around one,” said Dean as you broke off from him to head to the women’s room. By the time you got back out, Dean had a cup of coffee waiting for you and a candy bar. He’d remembered which kind you liked from the last time.

“Mmm, coffee,” you said, reaching for the warm cup as Dean chuckled. 

“Latte hun but close enough,” said Dean. 

“Coffee snob,” said Sam between yawns. He had a bagel in one hand while Dean held a bag in his other. “I made sure he got you something besides pure sugar for breakfast,” said Sam. You reached for the bag and found a breakfast sandwich inside.

“Even better, pure grease,” you said, unwrapping it and taking a huge bite. 

“That’s why she’s mine and not yours,” said Dean, throwing a lazy arm over your shoulders as you headed back outside. Sam rolled his eyes, probably able to spout off a million reasons why you were always going to be Dean’s, but he kept them to himself.

You you each took no more than a few minutes to devour you food and throw it in a trash bin in the parking lot, already piling back in the car when Sam pulled out his phone.

“Hi mom…a few hours…yeah, Y/N’s here too…Y/N is there anything special you want for dinner?” asked Sam as he turned in his seat. You shook your head no, not wanting to be a bother, you were sure whatever they were having was going to be fine with you.

“She likes steak,” said Dean to Sam as you dropped your jaw. Sam reiterated the information before you could stop him and soon he was off the phone.

“Why’d you do that!” you said, shoving Dean’s shoulder. “Now they think I’m some sort of spoiled brat,” you said, rubbing a hand against your head. You shut your eyes but found Dean’s hand on your wrist, lightly pulling it away.

“It’s always the kid’s choice when we come home for a break. Trust me, they know you aren’t a spoiled brat,” said Dean, making sure you caught his face before he turned back around.

“But I’m staying there for a week and-”

“Y/N, you’ve got to calm down. You were invited and that’s that,” said Sam, a heavy sigh in his words. You mumbled an apology as Dean started up the car again. It was like they said, you had both of them and their parents liked you, you had nothing to worry about.

 

“Home sweet home,” said Dean as you pulled into the familiar little cabin. Only it didn’t seem so little now, the other car in the driveway, not just you and Dean having a weekend away. You didn’t even realize until then that you’d never even ventured to the second floor where the kid’s rooms were.

“Love this place,” said Sam as he climbed out and you followed after. The air was much cooler now, no swimming this time around although you suspected a backyard fire was still a likely occurrence.

Sam grabbed his bags with ease as you put on your backpack, your duffle was heavier than you thought but you shrugged Dean off and told him you had it. You were almost in a full blown sweat when you knew you should have changed into jeans and something less lazy day-ish to meet Dean’s parents again. You looked like a bum, barely able to carry your own things, maybe you could sneak off in the middle of the night if it came to that.

“Sammy!” you heard a happy voice squeal as it opened the front door. You watched Sam disappear inside and receive a big hug from first his mother, then father as you trotted along behind him, Dean following you. Soon she was giving you a big smile as you managed to bring your bag in with a thud and slip your backpack off.

“Hi, Mrs. Winchester, Mr. Winchester,” you said, turning to each of them and giving them a smile. You were a little surprised to find yourself pulled into a big hug by her and then by Dean’s father as well.

“That’s John and Mary, kiddo,” said Dean’s dad as you looked on a little dumbfounded. 

“And you made her carry her bag! Dean!” said Mary as Dean rolled his eyes.

“Told you to let me take it,” he said, staring at you as he received hugs as well.

“Independent, I like it,” said John who stood beside you. He took a step to lift up your duffle and you felt a little better when you saw someone like him struggle. “Strong too,” he said with some effort before setting it down again.

“Guys…” you heard Dean say as his cheeks began to flush pink. Mary was already moving into the kitchen offering drinks as you were handed a glass of water.

“Obviously smart. She dressed for comfort for a seven hour car ride unlike you two,” said Mary, pointing to Sam and Dean’s outfits. You smiled to yourself as you knew your fears had been stupid all along.

“That’s not fair, I picked out her clothes this morning,” said Dean, crossing his arms. John and Mary blinked rapidly a few times as Dean realized what he’d said. “I didn’t mean…what I meant to say-”

“You on the pill, Y/N?” asked Mary and you saw Sam physically cringe at how the conversation had turned.

“Yup,” you said, barely squeaking out the word. 

“You wrapping up kid?” John asked Dean. Dean threw a nervous glance to you and John almost groaned. “Well Deanie’s never been with no one else so as long as you’re good kiddo, I suppose you’re okay. But start wrapping up for her sake, ya idiot,” said John, Dean nodding absentmindedly.

“Kill me now,” said Sam as the awkward silence filled the space.

“What are you complaining about, ain’t like you’ve ever been with a girl-”

“Dad!” yelled Sam as you and Dean chuckled. 

“He’s probably just waiting for someone he loves,” you said, giving Sam a soft smile.

“God knows Dean did,” said John as a mixture of embarrassment and pride filled you.

“No more talk of this, okay? Let’s get the kids packed away and then have some lunch?” said Mary, the voice of reason. This time Dean grabbed your duffle as you trotted upstairs, John following after.

“Boys, you take Sam’s room, Y/N, you can have Dean’s,” said John. You and Dean only shared a glance but nodded. You’d never spent that long without touching one another but you could survive somehow.

“Thanks, John,” you said, sliding your backpack off as Dean placed your duffle on a chair and turned to leave. John rolled his eyes.

“I was joking Dean. I already know you two have been going at it. Be safe and try not to disturb your little brother’s sleep too much but otherwise, do whatever the hell you want to each other,” said John, Sam groaning as he caught your eye.

“Too bad, I thought it might have been a little fun to try and sneak around,” said Dean to you, seeming to forget his father was also in the room.

“Could ya keep him in line for me, kiddo?” said John to you with a kind smile.

“I always try,” you said, John leaving the three of you to settle in before lunch. “Does he know my name?” you asked when you thought he was out of earshot.

“Course I do, Y/N,” you heard John say from down the hall. “But I like kiddo. We got Sammy and Deanie and you makes kiddo. Makes it easier to keep the illusion of authority in place when you guys are adults. If it bothers you…”

“No, no. I like it,” you said as you heard John let out a hearty laugh. 

“Your mother will kill you if you screw this up, Deanie,” said John as Dean groaned behind you.

“I think my family likes you more than me,” said Dean, tossing his bags next to yours.

“Oh, we do,” said Sam with a shit-eating grin. Dean responded by slamming his door shut and shoving you on the bed.

“What are we going to have to do about that?” he said, lowering his body over yours, rolling his hips just barely but stirring something in you that made you whine.

“But lunch…” you said, Dean’s hand tucking it’s way under your sweatpants, past the underwear he’d picked out that morning and making a straight shot for your clit.

“Don’t worry,” he said as you gasped quietly, his fingers harsh against the bundle of nerves, twiddling it and rolling it fast. “I know what I’m doing,” he said, one of his hands coming up to cover your mouth as you had trouble keeping quiet. “I’m going to get you close, get you so close, little girl,” said Dean, your hips bucking upwards as Dean’s thigh pinned yours down to keep you still. 

You couldn’t help but moan, come undone under him. You wanted to scream, shout his name with how fast he was going at you but his strong hand clamped over your mouth kept you silent, something about being helpless under him turning you on even more.You were so close as your hands squeezed his wrists, telling him you wanted more. Then he pulled away, leaving you horribly empty.

“What do you always say? I’m such a tease,” he whispered as he leaned in close, a whimper barely heard under his hand still covering you. “You’re going to have to learn to be quiet sweetheart or get used to something covering those pretty lips. But God if you aren’t the sexiest thing I’ve ever seen like this,” he said, taking a moment to memorize the way your looked under him before pulling his hand away and kissing you gently. When he broke away you made your eyes hard. 

“You think you’re hot shit, don’t you?” you whispered, his frame towering over yours as he caged you in possessively.

“I’m going to make you cum harder than you ever have in your life this week sweetheart. My family might think you’re some sweet little thing but I know what you are,” said Dean, nibbling at your ear, winding you up again.

“And what’s that?” you breathed, unable to get an angle to grind against him and finish yourself off.

“My dirty little girl. You’re going to be begging for my cock by the time the day is over,” he growled against you, sending vibrations through your jaw. You would have protested but his lips latched onto yours, his hand diving back into your pants as he thrust two fingers inside you curling them as he made long drags against you. 

You screamed into his mouth, the sound muffled to barely anything as you withered under him, your orgasm crashing over you. Dean barely let you enjoy it though before he was pulling out and sucking on his fingers.

“Delicious,” he said with a cock of his eyebrows. You couldn’t help but stare at him in the way that made him smirk. “Good girl, you know who you belong to you.”

“And you know who own’s you,” you said, sitting up on your wobbly knees, letting yourself lean over him. “Two can play this game, Frat Boy,” you said, pushing his shoulders back so he lay flat on the bed.

“Kids! Lunch!” you heard Mary yell from the floor below. You growled as Dean caught a break and sat up again. You stood but made sure to give him a nice pat on the lap, making him jump before you left the room.

“You’re gonna pay for that later,” said Dean to you, Sam exiting his room at the same time.

“Keep the dirty talk in the bedroom,” said Sam to Dean as you walked backwards giving Dean a little cock of your head. That was until you saw both Dean and Sam rushing forward, arms reaching for you and grabbing you as you felt the ground fall away behind you.

“Careful,” they both said, Dean’s tone a little more serious than Sam’s playful one. 

“If you crack your head open we can’t have fun,” said Dean, turning you around so you faced the stairs and placing an arm around your waist. Sam probably saw it as Dean being his normally cuddly self but you could tell from the grip he had on you he’d gotten scared.

“I’m okay,” you whispered to him as you got to the landing and headed down the last portion of steps. You felt his head nod as he relaxed, Mary and John waiting patiently for the three of you.

 

It’d been nearly a week since you’d been at the cabin with Dean and his family. Thanksgiving had finally arrived and you knew more family members were coming today. But honestly, you were ready to snap.

Dean had been the most perfect, wonderful, attentive boyfriend in the world over the past week. He’d managed to bring you into family traditions without making you feel uncomfortable, knowing you had your own reservations about celebrating a holiday again. You’d been hiking and had campfires, even pitching the tent in the backyard again, helping Mary cook and making Dean another pie.

But at night, the time Dean was yours and yours alone…the boy was trying to kill you. You hadn’t come once since Dean had pinned you to the bed that first day. Friday night, he’d pounded into you so hard you thought you’d break the bed, but pulled out before either of you came, neither of you getting a release. Saturday, he played with you during your morning shower but not nearly enough. That was when he told you all about his torturous plan.

“You better not finish yourself off,” said Dean, an edge to his voice. You blinked curiously at him as you wiped yourself dry in your room.

“Are you telling me I’m not allowed to cum?” you asked, a scoff in your voice. Dean’s gaze hardened, authority in his green eyes.

“That’s exactly what I’m telling you. You don’t cum this week unless I let you,” he said, stalking over to you, naked and still wet. You had raised your eyebrows but sank to your knees. If you took him right now, no way in hell would he live up to that.

“Is my good little boy misbehaving again?” you taunted, your hands grasping his hips. His hands found yours though and pulled you up. One look in his eye told you he wasn’t kidding. “Dean…” you said, a little too needy. He only chuckled at how desperate you were for him.

“Touch all you want but don’t cum. I want to see if you can do it. I might just give you something you’ve wanted in return,” he said low, his hands on your ass, spreading your cheeks apart. You dropped your head against his chest.

“Fuck, why am I so pathetic around you,” you whined, resolving yourself to follow his orders. A gentle hand under your chin brought you up to meet soft eyes.

“You aren’t pathetic, Y/N. It’s supposed to rile you up beyond belief. I’m sorry. We don’t have to and I shouldn’t tease you like that anymore. I said I wouldn’t and-”

“Shut up Dean. I like it and I like when you push me. I’m just so easy around you I don’t know why,” you said, giving him a reassuring smile.

“I think it has something to do with loving and trusting me,” said Dean. You nodded against him when a spark of an idea came to you, one that you both regretted and wanted to be a reality.

“Dean?” you asked, his head popping up at the tone.

“You’ve got something dark and twisted going through that head of yours,” he said, watching you bite your bottom lip.

“If you really want to push me, then push me. Touch me, all day, everyday. Fuck me so I should be screaming your name, so I’m begging you to let me cum. Do it over and over and don’t let me until you’ve decided it’s time,” you said, looking up at him through your lashes. Dean grew hard against your leg at the mere thought, the idea of you giving him such control turning him on.

“If that’s what you want,” he said, hands trailing to your hips. You didn’t need to speak as he saw the answer in your eyes. This time he dropped to his knees, slowly kissing your body on the way down. Your hand fisted in his short hair and gave a tug, pulling a moan from him. 

“You on the other hand, I’m going to make you cum without touching you,” you said, seeing his cock twitch as you pulled a little harder. Dean’s face scrunched up against your stomach, pressing his lips against your skin to stifle the whimper that left him. You smiled as you did it some more, glad that he was giving you this level of trust to see him exposed beneath you.

Dean breathed hard against you before latching his lips around you clit, sucking hard, all the while you played with his hair. You had to use one of your hands to cover you mouth, the ferocity with which Dean was going down on you too much. His hands helped you stand as your body quaked but soon you felt one leave the back of your thigh and tap your wrist.

“Too much?” you asked, afraid you’d hurt him with the little tugs. His gaze lifted towards yours, his lips wrapped around you clit, on his knees and you could only imagine this was how he felt when you sucked him off.

“Harder. I like it harder. I’ll tap you if I want you to stop,” he said, breaking away only to give those few words before his tongue was buried inside your heat again. You weren’t positive about being that rough with him but he looked up with pleading eyes and you were done. If he was going to decide the next time you came the least you could do was give him a little pain with his pleasure.

Dean inhaled sharply against you as your fingers twisted in his hair and pulled. Hard. You were guiding him at first, even if he didn’t need it, even if you knew you wouldn’t get to come, but you were getting high on something else. Power.

Dean’s mouth was moving on you in ways you’d never seen before, his face contorting in pleasure as you ripped and pulled and tugged at his soft strands, still damp from the shower you’d shared, sticking up from where you had been fisting your hand in it hard. You could see how swollen Dean was, how much he wanted to be touched so you let yourself trust that Dean would stop you if it was too much for him.

Dean was whining and whimpering now, muffled but you saw it in his eyes, in the way his body wriggled and needed attention. He didn’t care about being the one in control as you pulled hard, so hard he was trembling with the effort it took not to come. You didn’t want him to hold back, you wanted him to come like this and you went for it, pulling hard and long against his beautiful hair as Dean moaned against you, his cock twitching violently as he came on the floor.

You’d almost forgotten how sensitive your own body was, how close you were when Dean pulled away, you weary body carefully sitting on the edge of the bed as Dean sat on the floor leaning against it. You were panting hard, the sound of your exhales the only sounds to fill the room as you came down from your non-release, as Dean calmed through the aftershocks of his orgasm.

“Shh, baby,” you cooed to Dean, running a soothing hand through his hair. He was still shaky as you saw he wasn’t looking at you. “You okay?”

He turned to look up at you with hazy eyes, lost in the pain/pleasure he’d had, but something a little submissive in them as well. 

“I didn’t hurt you?” you asked, continuing to give his head a massage, Dean’s eyes fluttering under your touch.

“No, no that was amazing, thank you,” he said, his pupils blown but coming back into focus now.

“I like taking care of you,” you said absentmindedly and felt Dean stiffen beneath you. You stopped moving your hand, leaving it to rest in his hair as Dean began to take in how you were the big one, the dominating one right now, the one you didn’t think you’d like to be. “It’s okay if you liked me like that ya know,” you said, running your hand through his hair again.

Dean’s mouth parted as he looked at you curiously, like he was deciding something. You didn’t push him to talk, only gave him the comforting strokes of your hand as he shut his eyes before turning back to you.

“You know we haven’t talked about…stuff we like…” he said, almost a little ashamed.

“You mean kinks?” you said with a soft smile. Dean nodded as you laughed. “I think hair pulling is one of yours, Dean,” you said, noting how he’d been the one to turn to mush under you from just the simple act.

“Yeah,” he said, his face pink from embarrassment and over heated body. “I think we’re ready to go to that next level,” he said. You leaned over to kiss the top of his head.

“I’ve got an idea,” you said, reaching for his hand so he’d sit on the bed beside you. “After break, after finals week, we spend winter break doing whatever we want. No judging, no pressuring to do something if the other doesn’t want to, we learn more about each other,” you said. “And more about what we like too.”

Dean smiled as he held your hands. 

“Gonna make me wait two whole weeks?” said Dean, knowing finals week was right after you got back from break. 

“Yeah but then we have six weeks to do anything. No pesky classes or homework. Just you, me and my apartment,” you said, givng him a grin. Dean licked his lips but tsked you.

“One fatal flaw in your plan, Y/N. See, you’re spending winter break at the Winchester’s. Now that might mean a couple week’s alone up here before the holidays or it might mean my house but you are most certainly not spending break apart from me,” said Dean. A week for thanksgiving was one thing, a friendly invitation, but over a month? What would his family think? “I wasn’t asking, Y/N.”

“I don’t want your family to see me as the clingy girlfriend Dean,” you said, watching his features become hard.

“Stop caring about what they think. I want you with me and you’ve told me more than once you’re mine so start acting like it. You are spending winter break with me, understand?” said Dean, obviously pissed. But he softened, seeing something in your face he didn’t like. “I’m sorry, I don’t,  _own you_. I know that. I just don’t want to spend all that time away from you, want you to be alone. I’ve seen you with my family yesterday. You’re happy. I thought…” he said, trailing off. You smiled to yourself as he searched for words. He was always looking out for you.

“I’d love to, Dean. Partners?” you asked, reaching out a hand to cup his cheek.

“Partners,” he said back shyly, giving you a smile. You sat in silence for a moment, letting the sweetness between the two of you fill the room before it became unbearable.

“So about those kinks?” you asked, breaking the silence so he wouldn’t have to. “Maybe you make a list, I make a list, we share, a little of this , a little of that, a whole lot of cumming, whole lot of sexy times with my Frat Boy?” you asked, giving Dean a kiss. 

“God I love you,” he mumbled against you, his hand finding your clit, barely grazing it before pulling away. “It’s not on the list but teasing you is definitely one of them,” he said, swinging his legs off the bed to stand.

“Oh, I noticed, babe,” you said, standing yourself. Dean gave you a wink before leaning in close.

“We’ll share tonight?” he said, telling you to think up what you wanted during the day. You nodded as you watched him dress, not sure how you were possibly going to wait to find out what his were, let alone the week ahead of you.

 

“Ready?” said Dean, eager as he sat in bed next to you that night holding a folded piece of paper. You turned to him, sweaty and naked under the blanket, a puppy dog look on your face. You’d been so close and denied again. “Hey, it’s Saturday night. You’ve only got to make it to Thursday before I give you what you want,” said Dean, his hand reaching under the cover to play with the skin of your inner thigh.

“Someday I hope to endure this kind of punishment on you,” you said, reaching over to the night stand to grab your paper. Dean only laughed as he threw an arm around your shoulder, sitting the both of you upright.

“Best part is, wasn’t even a punishment. I asked and you asked me to push you, way harder than I was going to by the way. Your own fault really,” he said, pressing a kiss to your temple.

“Let’s just share these already, would ya?” you said, reaching for Dean’s sheet as you handed him yours. Carefully you unfolded it, hearing Dean do the same. 

You nearly came right then and there, Dean’s hand on your thigh pulling back up as if he needed both his hands on the sheet to read it. 

“Wow,” was all you could say, Dean remaining silent beside you.

“Uh huh,” he said, eyes flickering over the page. “No judging remember?” he said, trepidation in his voice. 

“Dean?” you asked, committing his list to memory. “You really want this? I mean you really want #4?” Dean nodded before tapping his finger on your sheet.

“#3? You’re sure about that?” he asked, eyes a little wide. You shook your head. “Well alright then. As soon as break starts, we’ll start with one of yours,” he said, taking both sheets and folding them together, placing them on the nightstand out of harm’s way.

“One of mine?” you asked, watching Dean chuckle.

“Ladies first,” he said. You shut your eyes as you murmured your ‘I love you’ and ‘goodnights’ to one another, the image of Dean’s list in your brain, of your list in your brain, flashing through your mind. 

Dean’s little game of not coming would be nothing compared to that list.

 

For the next five days, Dean was relentless with you, so much so that you knew you’d be a begging mess as soon as Dean got you in the bedroom that night.

“You got your eyes hooked on that boy like glue,” said Dean’s Uncle Bobby, who wasn’t really his uncle but still was like one to him. You nearly spat your wine back in the glass as you looked up at him. “Just saying.”

“The kids are in love, leave ‘em be,” said Jody as she wrapped an arm over Bobby’s shoulder. Glancing around the room, you’d realized early on that family didn’t necessarily mean by blood to the Winchesters. Beside the Winchester clan itself, everyone else was a family friend. Bobby, Jody, Donna, Charlie, and then the unexpected, several of the frat guys showed up. Cas, Chuck, even Gabe.

“Eleven, Twelve, okay, everyone’s here,” you heard Mary say to herself as she counted heads in the room. Looking around you heard voices and laughter, warmth and people reconnecting. You sat your glass down on the counter as you took it all in. A strong pair of hands wrapped themselves around your waist and tucked you into the kitchen.

“You okay, sweetheart?” asked Dean, leaning his head against yours. You couldn’t find the words as you titled your head up to look at him. “Is it too much?” he asked quietly, knowing he’d pull you away in an instant if you needed him to.

“I like having a family again,” you said, leaning back against him, letting a smile fall over your lips. Dean held you, letting you take it all in in the safety of his arms. A footstep behind you turned the two of you around to see John and Mary watching you.

“We like having you too kiddo,” said John, a blush coming to your cheeks. “Dean kind of told us about…asked us to keep an eye on you if you got overwhelmed,” said John, noticing that he was holding Mary very much in the same way Dean was holding you.

“He’s very good to me like that,” you said to his parents, feeling Dean squeeze you a little tighter at your words.

“So you’re spending winter break with us?” Mary asked hopefully. You could actually  _hear_  the hope in her voice and you practically broke. You nodded, not trusting your voice as they gave you reassuring smiles. “And can we guess summer break?” You turned to Dean who only smiled.

“Forever includes next summer sweetheart,” said Dean, your head dropping in case you started crying. “Mom, stop looking at us like that,” said Dean, his head tucking yours underneath it, forcing you to look up.

“You found your person. I’m sorry I’m happy for you two,” she said, feigning hurt. You squinted your eyes and knew Dean must have been doing the same.

“Try walking in the room with the two of you. You’d know that you’re a done deal if you could step back and see yourselves,” said John. 

“Stop with the mush guys,” said Dean, a little whine in his voice but not the one you were used to. You nudged him slightly.

“Thanks. We should help set the table,” you said, eyeing Dean’s parents. 

“Kiddo gets first pick of pie,” said John as Dean reluctantly let you loose. 

“She doesn’t even like pie!” said Dean, both John and Mary staring at you with wide eyes.

“He really loves her if he looks past that,” said Mary to John. 

“Oh my God, give me the plates so I can go set up!” said Dean, grabbing them off the counter and walking across the room to the dinner table. John gave you a nudge as he caught your smile.

“Told you,” he said, holding out his hand for fist bump which you returned before giving him a high five in response. Dean stood upright, watching from the other side of the room. “We bet she could get you to help set the table for once,” said John, pointing down at you. Dean eyed you mischievously before returning to his task. “Did I get you in trouble?”

“The good kind,” you said absentmindedly before realizing this wasn’t one of the frat boys, it was John Winchester. “Um…”

“Got to help my boy out somehow,” said John, ruffling the top of your head. You glanced at Mary who looked ready to kill him.

“That is your future-”

“Y/N, get over here or away from them or I won’t make it through dinner,” said Dean as you scurried towards him, throwing John a smile.

“I see where the cockiness comes from,” you said as you grabbed some plates.

“Should I extend our arrangement another day?” Dean whispered threateningly in your ear. You gulped and shook your head. You knew you wouldn’t last another night. “Good girl,” he whispered again as a timer went off.

“Alright people! Grab some grub, grab a seat and let’s eat,” said John, his voice booming over the group as people began to grab plates from the table and form a line. You and Dean took up the rear, but that was okay with you, coming back after loading up with the best meal you’d had in years to find two spots next to each other in the center of the table.

“Happy Thanksgiving,” said Dean to you, his voice soft. 

“Happy Thanksgiving,” you said back, already aware of everything you had to be thankful for that year.

 

“Fucking hell, Y/N,” Dean groaned low, your fingers digging into his wrist as you screamed under the hand that was clamped over your mouth. You rode that wave of pleasure long and hard as your heels dug into Dean’s ass, pressing him deeper into you as you finally enjoyed that sweet release. You could see Dean start to break and flew your small hand up to cover his mouth, his grunt muffled under you. You kept each other quiet as you kept going, kept pushing straight into another orgasm. After almost a whole minute you went lax, your grip on Dean loosening enough for him to pull away.

“Worth it,” you breathed out, telling him his little game had satisfied in all the right ways.

“I can’t wait to get you alone so I can hear the beautiful sounds you make again,” said Dean, his body limp under yours as you could feel the effort it took for him to pull the covers over you.

“You’ve got finals coming up. You have to study,” you said, glad you only had final papers this semester. Dean huffed.

“Are you telling me I get nothing until after my finals are over? It’s…two in the morning on Friday. I have to wait until next Thursday? A whole week?” he asked in disbelief.

“You can touch yourself, just don’t cum,” you mocked, Dean groaning beside you.

“This is my payback, isn’t it,” he said, eyes shut. You ran a hand over his chest as you cuddled against him.

“I want you to do well. Besides, we’ll both be well rested for what’s on that list and we both know we’re going to need it,” you said, wondering which one of your kinks you’d be trying next Thursday.

“Can’t wait,” Dean mumbled next to you, sleep catching up to him. “Y/N?”

“Mhm?” you hummed, letting yourself drift away.

“Next Thursday, when we’re back in this cabin, just the two of us for two, three whole weeks…” he said, a little cockiness sneaking through.

“Can’t wait,” you said, Dean’s hand finding your waist, giving just a small squeeze before letting it sit there. “Night,” you yawned, turning into him.

“Good night sweetheart,” said Dean, his lips against your forehead the last thing you remembered before falling asleep.


	13. Chapter 13

**Summary for the Chapter:**

> Dean and the reader finish up the semester before heading off to spend winter break together…

Dean was staring at you like a puppy dog, down on his knees in the middle of your kitchen, hands on the backs of your thighs, hands dipping underneath the bottom of your pajama shorts. You knew what he wanted, what he so desperately wanted. But you had plans. This time, after seeing that list of what he wanted to try, you had the confidence to be okay with turning him into a groveling mess.

“When we get back to the cabin tomorrow, good little boy,” you said, ruffling his hair and giving just the smallest of tugs before letting go and walking back a step. To your surprise, Dean stayed there on the floor, staring up at you obediently.

“You said after finals. I’m all done. Please, I haven’t touched your beautiful body in a week,” he whined, a small little surprise running through you that he was concerned about your needs rather than his own.

“Don’t beg Dean,” you said as you leaned down to his ear. “It’s unbecoming of you,” you said, pulling his earlobe between your teeth, teasing him. You pulled back and headed towards your room, Dean pouting on the floor behind you. “The sooner we go to bed, the sooner we can get up and drive up there tomorrow,” you said, your words snapping him out of his haze as he shot up and sprinted past you into your room.

“Then get your perfect ass in here so we can head out at five,” he said, patting the spot next to him. You didn’t waste anytime to crawl in beside him, feeling the familiar weight of his arm over your waist. “Did you do your homework this week, Y/N?” he said low in your ear.

“I told you, you’d take care of your finals and since I didn’t have any, I’d take care of the other stuff,” you said, nodding towards the smaller black duffel you’d bought a few days earlier, along with all the goodies inside that made you wet at the mere thought.

“And you got everything? Packed it all up?” he asked, knowing that bag would not want to be left behind. You had two whole weeks at the cabin by yourselves, two weeks with Dean’s family up at their actual house, a week with Sam and Dean at the cabin and another to just the two of you up there before the spring semester. Six weeks of pure bliss.

“Well one package was a little big,” you said, grinding your ass against his flaccid cock. “Thought I’d let you take care of that one,” you said, turning your head with a little smirk.

“I can’t wait for tomorrow,” he said, nuzzling his head against yours. “Just me and you,” he murmured, sleep starting to get to him despite his excitement. “Just me and my sweetheart.”

“I love you,” you whispered goodnight.

“I love you,” he mumbled back, soft snores falling from his lips, lulling you away.

 

“Dean!” you giggled, his hands had you pressed up against the back of the front door, your bags tossed lazily inside.

“We’re at the cabin, I thought you’d finally stop teasing me,” he said, lips sucking and pulling at your own. You would have loved to just do what you wanted right then and there. But you still had your plans.

“Down boy,” you said, pushing him away and finding a sad look on his face. “We unpack, lunch and then…” you said, walking up and getting in his face, “Ladies choice I believe it was,” you said with a wink.

Dean wasted no time in getting your things into the master bedroom, the king size bed more than a step up from the full you’d been forced to share during your last visit. You’d changed into one of Dean’s sweatshirts and threw on your lazy sweatpants, watching Dean crank up the heat and start a fire as you made lunch for the two of you. 

“Pacing won’t get you anything faster, you know,” you said, the sounds of his bare feet along the wood floor telling you how bad he needed you.

“Y/N, I-”

“Eat up,” you said, sliding him a sandwich on the counter. “You’ll need your energy,” you said darkly, taking a large bite of yours and making a show of licking your lips. You were laughing hard as he ate the whole thing in only a few bites. “I’m taking my time,” you said, taking slower bites, his eyes constantly on you.

“Y/N,” he said, voice full of need as you could see he was starting to get hard in his sweats. You made sure to clean everything up, wash off your hands and take a long walk around the downstairs, smiling to yourself as you saw Dean try to figure out what item on your list the two of you were about to test out.

The snow had fallen some, the place quiet as you had a good understanding now that this little cabin was miles and miles away from anyone. A perfect romantic spot. The sky was gray as a little snow shower fell out the windows, the cold contrast outdoors to the warmth inside a happy reminder of why you had also fallen in love with the place.

“Y/N,” he said, a little crack in his voice. You turned your attention back to him, walking close as you walked to the kitchen table, pulling out a chair and dragging it into the open space of the living room, a little bit of heat of the fire reaching the spot.

“You said ladies choice and I pick something from your list, Dean,” you said, walking over to him and taking him by the hand. You led the two of you into the bedroom where you instructed him to strip, doing the same yourself. “Go sit in the chair,” you said, watching as he still wasn’t sure what you were going to do. When he was out of sight, you went to the black duffel in the master, pulling out two things, hiding them behind your back as you left the room. Dean had listened and was sitting patiently in the chair, his cock hard and swollen, precum leaking heavily from his slit.

“What are we doing?” he asked nervously when you were finally stood in front of him. You raised an eyebrow as you revealed the items in your hands, watching Dean’s jaw drop slightly as he knew which kink you were trying out.

“ _I want Y/N to blindfold and tie me up…and do whatever she wants to me_ ,” you recited from memory. Dean’s cheeks flushed a little. You’d known this was coming for a while, Dean had always implied he’d liked to be teased by you. You just hoped you delivered.

“I…I…” Dean stammered when your hand found his cheek.

“You’re always going to be my big strong, Dean,” you reassured him, seeing him relax. “But today, I call the shots, understand?” 

“Yes,” he said, voice hoarse. “Please,” he said as you smiled. You picked up the silk scarf first, staring him down. You said nothing as it finally registered with him what you wanted, his hands going behind the back of the chair. “Good little boy,” you said, seeing a flicker of desire in his eyes. Behind his back, you tied the silk to one wrist and then the other, giving him just enough room so his shoulders hopefully wouldn’t hurt too much. You saw his hands curl into fists as he pulled against it, then pulled hard and harder still. A shocked sigh left his lips as his chest started to rise and fall faster.

“Is that how you wanted to feel?” you asked, walking in front of him. He nodded, his arms still straining. “Remember the word?” you asked, hoping he was enjoying the feeling a being restrained and not actually scared.

“Yes, I know the word but I don’t need it. I like it, I like this,” he said, breathing harder than necessary, his pupils blown. You took that as a sign to place the blindfold over his head and take a few steps back to admire him. Fuck you could do anything you wanted and he had to take it, would never know it was coming. “Y/N?” he asked, a small sheen of sweat covering his skin.

You stayed quiet, seeing his body build with anticipation, his chest puff out, his lips part, his cock so swollen and needing to be touched. You took the few steps over and ran a hand down from his throat to his stomach, stopping just before his cock. Dean shuddered at the touch, hips arching up, silently begging for more.

“I teased you all week,” you said, working both hands over his chest, along his arms down to his tied wrists, running along the inside of his bare thighs. “Do you want me to tease you Dean?” Your hands ran over the V of his hip bones as you saw him bite his bottom lip. 

“Please,” he whined, so desperate and needy and exactly the answer you were hoping for. You rubbed your thumbs close, so dangerously close to the base of his cock before pulling back. “Y/N,” he whimpered, hips trying to move as you held them down.

“You asked me to tease you, Dean. You even said please,” you said, moving in close as your hot breath spread over his face, watching him momentarily forget how to breath. Dean was beyond words, now letting whimpers and whines escape him with no shame. “Tell me what you need.”

“You, fuck I need you. Something, anything, please,” he said, dropping his head as he strained again. You chuckled, never once thinking you’d break him so easily. “Y/N, I’m begging you, please I need-Oh fuck!” he yelled, so lost in his own need that he hadn’t felt the shift of the air as you straddled his lap and sank down hard.

“I’m going to take good care of you,” you said, rocking your hips forward, a strangled moan falling from him. Fuck, you were so turned on, Dean had never made those noise before. Your hands braced against his shoulders as you lifted off and sank down hard, setting a grueling pace you knew he’d never be able to last with.

“Y/N!” he cried out, coming after only a few minutes. But you were going to push, let yourself push him harder than he’d ever gone before. “You gotta slow down-”

“Make me. Oh wait, you’re a little tied up at the moment,” you interrupted, riding him hard as he started to tremble, your own orgasm growing inside. His head was dropped on your shoulder, taking what you were giving, half-moans and half-profanities falling from his lips. He was still hard inside you, still twitching as you felt yourself get close. “Dean, I’m gonna…”

Dean screamed, actually screamed as your orgasm hit, your walls gripping him so tightly you felt him come again, his cum filling you as you rocked your hips hard, squeezing everything you could from him. He was whimpering in pleasure when you finally climbed off, kneeling in front of him. Your legs were wrecked but you knew you could give him one last treat. Spreading his legs wide, your lips found his sensitive cock, taking his tip slow and then the whole thing, pausing to relax before letting him slip down your throat. He became hard again inside you, everything in him reaching for something, needing you more than he’d ever done so before.

Again Dean was yelling as he came, your lips tingling as you swallowed him down, so full of your Dean. He was shaking as you climbed back to his lap, giving him a slow and sweet kiss he wasn’t expecting. You stayed there with him, letting him calm before you took the blindfold off.

“Everything you were hoping for?” you asked gently, seeing him adjust to the light as you saw the euphoric haze in his beautiful green eyes.

“Yes, more than…thank you, that was incredible,” he said, a tired smile on his face. “But I need a break before anything more today or else you’re going to kill me,” he said, still a small little quake running through his body. You leaned in and gave him another kiss before climbing off, undoing his restraints and climbing back on his lap. Your hands massaged his shoulders, and arms, all the way down to his wrists that were a little red from his struggling.

“I’d never want to do that,” you said, running a hand through his hair. You could see it in his face that he was exhausted, lost in bliss, eyes looking at you, waiting for you to tell him what to do next. “Come on, let me get you in the shower and in bed for a nap, you need it,” you said, placing an arm around him as one of his was thrown lazily on your shoulder.

“Thanks for that, Y/N, really,” he said, leaning on you. “It was…I liked letting you have that over me, knowing I trust you to see me like that, make me like that.” You smiled to yourself as you led him to the shower, helping him inside. “Thank you for taking care of me too,” he said, a shy smile on his face as you turned on the water for him.

“You never have to thank me for that, Dean. It’s my job to look out for you, just as much as it’s yours to do that for me,” you said, picking out some towels for him, leaving for a moment to find him some pajamas to change into. Dean looked like he’d regained some of his senses by the time you’d returned but he had a cocky smile on his face as well.

“After my nap, I get to pick something on that list,” he said, knowing he already had something in mind for you. 

“Can’t wait,” you said, leaving him be. You used the kids smaller bathroom to wash up, giving yourself some space. By the time you’d come back downstairs, Dean was changed and in bed, passed out on top of it. You smiled as you placed a blanket over him, taking a moment to take in how peaceful he looked. You changed back into your clothes from earlier as you cleaned up the living room, placing the items back in the duffle as Dean was sound asleep.

A few hours later you were curled up on the couch with a book, the gray outside turning to night despite it only being a little after five. The warmth of the fire and occasional crackle were perfect distractions as you waited for Dean to recover. Such perfect distractions you didn’t even hear him come up behind you, his hand playing with a few strands of your hair the only thing alerting you to his presence.

“How’d you sleep, Frat Boy?” you asked, shutting your book. Dean’s hand stayed near the back of your neck, running slowly along the skin.

“After dinner, you’re gonna be the one fucked so hard you forget your own name,” he said, his hand trailing up to fist in the back of your hair hard for only a second. “Number 2 in case you’re wondering,  _your number two_ ,” he said, walking away to head into the kitchen.

You spun around quick, eyes wide as Dean turned to smile darkly. “I’d enjoy dinner, sweetheart. You know what’s coming after,” he said, turning away. You stood and practically came right there. Number two, that was the one you thought he would never try, would never do to you but hoped and prayed he would.

“You’re going to ruin me,” you said to yourself, staring in his direction.

“Oh I plan on it,” he said with a wink. “I absolutely plan on it.”


	14. Chapter 14

**Summary for the Chapter:**

> Dean gets his turn at trying something out from the list…

Dinner went by slow, exactly how Dean wanted it. He’d had his fun earlier, letting you be in charge and all, but now it was different. One of your ideas was up this time and you were feeling that rush of doing something you wanted to try.

“Sweetheart?” asked Dean when you realized you’d zoned out, the plates cleared away, the leftovers packed up for tomorrow. “If you’ve changed your mind, that’s okay.”

“Do it,” you said back confidently. Dean smiled as he stood up. “Unless you don’t want to,” you said, his gaze already turning dark as he curled his finger, telling you to stand.

“ _I want Dean to let loose and be primal, to not be concerned with what I’m feeling and focus solely on himself,_ ” said Dean from memory. “You don’t want me to hold back, be as rough and punishing as I want, not give a damn about your own pleasure?” he asked, taking a step beside you to whisper in your ear.

“Yes, Dean. I want you to have that,” you said, biting your bottom lip. “Don’t worry about me.”

“Anything for my sweetheart,” he said, pulling away. “Go finish your book,” he said. “I’ll be back in a few minutes.” You watched as he walked away and into the bedroom as you understood the need for him to be alone for a moment. Even when the two of you hadn’t been quite together yet, Dean was always so very protective of you, even when he was dominating he held back, never wanting to push you aside. But you needed him to, needed him to think of himself first for once and let him know that you could give just as much as you took. 

You were able to finish the last few pages, put some more wood on the fire and shed your clothes by the time you heard the bedroom door open. You sat on the couch, hearing heavy footfalls approach from behind. They stopped, the sensation of someone standing over you abundantly clear. Tilting your head back you smiled as Dean looked down hungrily.

He said nothing as a hand found your throat and you gulped under it, his fingers feeling the movement of the muscles, a dark chuckle escaping him. His grip tightened a little, moving your head to fall back over the edge of the couch, his hard cock right there. Fingers squeezed your jaw, forcing your mouth open as Dean slid right in like he owned the place, not taking a second for you to adjust.

You tried to lick his underside, press the flat of your tongue against the large vein that ran there, knowing that drove Dean nuts. But one hand fisted in your hair, the other pressed over your throat in way that told you he owned you and he fucked your face. Fast and hard. There was no playing, no letting you tickle and tease. The drag of his cock against the back of your throat was intense, his hips thrusting into you deep so that your lips found his base every time.

Tears formed in the corner of your eyes but not from any real discomfort. You were loving it, loving how Dean was just using you, not caring at all how your throat would be wrecked from tonight. 

You were sure he’d want to keep going like this but with one simple pull, he was gone, cock and hands shifted away as you heard his footsteps walk around to the front of the couch. You smiled as you caught your breath, wanting to praise him but his eyes were completely blown. Dean was losing himself to this and you were dripping for him at the thought alone.

One of his hands grabbed your wrist and pulled you off the couch, dragging you roughly over to the fireplace before tossing you the ground, no gentleness it in. You laid on your back and titled your head up to see but found strong and unforgiving hands on your hips, pulling you forward and straight onto him.

“Fuck, Dean!” you moaned, his hands hiking your legs up over his shoulders, hands finding your breasts and rolling your nipples hard, his hips snapping into action as he drove in deep. “Fuck, fuck, fuck,” you groaned, your body going form 0 to 100 in nothing flat. It was too much, his pumps too deep, hands leaving bruises along your tender flesh. He fucked you hard, until you were shaking from not coming too soon, wanting to wait for him. When it was almost too much, he pulled away again, leaving you a panting mess on the floor.

Strong hands grabbed your hips again, slipping his achingly hard cock back in your needy pussy, soon reaching under your ass and lifting you off the ground as you hazily grabbed onto his shoulders. Seconds later, he had you pinned against the thick back glass door, the chill of it making you moan before Dean spun you and had you hiked up against the wall.

“Mine,” he growled, eyes boring into yours. “This is mine,” he said, squeezing your body as he thrust, your back sliding up the wall from the force of it. You nodded and whined under him as he continued his pace from before. Your heels dug into his back, slipping down to dig into his ass as your arms held around his neck for dear life. 

He was right, you were the one trembling now. You wanted to praise him, shout his name but you didn’t know what it was anymore, didn’t know yours. All you had was the bliss of being lost in pleasure, your head feeling like it was going to explode as every little touch of him on your skin sent sparks through you.

When Dean came in a loud, long, growling grunt, your whole body tensed, the pressure of him filing you with his cum breaking you. You screamed, screamed like your life depended on it as you clung to him, nails scrapping against his back so hard you’d drawn blood, your own back having nowhere to go as it arched, pushing him further into you if at all possible.

Your orgasm went on forever, aftershocks running through you as your mind went numb, the knowledge of kisses on your cheek and lips barely registering. Warmth tickled your skin as you were sat down by the fire and you felt Dean pull himself from you, your body swaying as something steadied you from falling. Hands you realized they were, pulled you down to lay against the sweaty body behind you, pillows and blankets there now. 

It took all the energy you had left to turn and face him, opening your eyes to see content but careful green eyes.

“ _That was fucking good_ ,” you told him, watching his trepidations fall away and a smile replace them.

“It was fun to let go, turn you into the same mess you made of me earlier,” he said, soft fingers running through your hair. Some trailed down to your throat, gently rubbing there.

“I’m good Dean,” you said, your throat not as bad as you’d thought it’d be. You both were silent for a few minutes, letting yourselves calm after the day you’d had. “You know…”

“We don’t have to do everything over break,” he said, seeming to read your mind.

“Pull it out when we feel like it?” you asked, Dean nodding in agreement that you could go a little slower with your list.

“I’m going to be touching you like crazy of course but…I’d like to do some cozy romantic couple crap with you over break too,” he said, no blush coming across his cheeks. You gave him a chaste kiss.

“You know, I saw a pretty big hill for sledding about ten minutes down the road,” you said, Dean laughing.

“That’s Sunday. Tomorrow we’re building a snowman and then I’ll throw a snowball at you, it’ll become a whole thing…” he said.

“And I’ll fall madly in love with you?” you said with a smirk. 

“I was hoping,” he said, the weight of his hand on your waist bringing you close to sleep.

“Sorry, can’t do it,” you said, watching a slight moment of concern cross his face. “I’m already madly in love with this guy, he’s a Frat Boy you see.”

“Oh really? Tell me more about my competition,” Dean said with a chuckle. You giggled.

“Ruggedly handsome, incredibly smart, hilariously corny,” you said, seeing Dean’s face beam. “Deeply loving, my protector, my best friend,” you said, seeing the glow in him grow stronger as you continued to speak. “My forever,” you said, pausing a beat. “He’s never letting me go so I’d just give up now.”

“Sounds like a great guy,” said Dean, face close to yours.

“He is and he’s mine. I just hope he knows how wonderful he is,” you said, mumbling against Dean’s lips. 

“He knows…but he likes to hear it from those beautiful lips every once in a while,” he said before giving you a soft and slow kiss goodnight. “Love you, Y/N.”

“Love you too, Dean,” you said, snuggling into his chest, falling asleep in a matter of seconds.


	15. Chapter 15

**Summary for the Chapter:**

> Dean and reader spend Christmas day together…

“Morning,” you heard the voice behind you whisper as you began to stir awake. You smiled as you opened your eyes, catching sight of the steadily falling snow out of Dean’s bedroom window. It was overcast from the looks of it, Dean’s clock showing it was just after 9. “Merry Christmas, Y/N.”

Dean’s soft lips pressed against your cheek, a smile in them. Without needing to ask, Dean loosened his grip enough so you could turn to face him before holding you close once more.

“Merry Christmas, Dean,” you said, pecking a short kiss along his scruff covered jaw. Together you stayed in silence, staring with sleepy eyes under the warm covers on the cold December morning. “I like my present,” you said, Dean squinting a little as he laughed.

“I didn’t give you any presents yet, sweetheart,” he said, tilting his head some. 

“Yeah you did, you just gave it to me a few months ago is all,” you said, curling your head as Dean tucked yours under his chin.

“Best present I’ve ever gotten,” he said, giving your body a gentle squeeze. You heard a laugh come from the hall, Dean’s grip on you tightening. “Go away Sammy.”

“Dean, be nice to Sam,” you said, squirming a bit under him. To your surprise, he only adjust his hands to keep you still.

“Using Y/N is not fair and you know it,” said Sam, stepping into Dean’s room. Dean had a puppy dog look on his face with just a little bit of that shit-eating grin thrown in for good measure. “Dad! Dean’s cheating!”

You heard a scurry of foot steps as John stepped through the doorframe, looking at Dean with his arms wrapped around you. He shook his head at his sons before sighing.

“Sorry for dumb & dumber, kiddo,” he said, as both Dean and Sam shouted in protest. “Family tradition. Sammy wakes up Deanie, drags him out of bed so they can open presents. It’s gotten a bit more physical as the years have gone by. Last year they wrestled for twenty minutes. Dean doesn’t like when his little brother can beat him,” said John, staring at the boys. You hummed before you gave Dean a sideways glance.

“Fine, let’s have at it,” said Dean, releasing you and pushing you to stand. You did, waiting near the door as both brothers stared each other down. “You know you can’t do it,” said Dean, tilting his head. Sam took a step away from the bed and then another.

“Yeah, but I can still get you out of bed in record time,” said Sam. He threw you a smile and before you knew it, was lifting you off the ground and throwing you over his shoulder.

“Hey, that’s mine!” said Dean as Sam ducked down the hall and scuttled down the stairs. You were already being set down in the living room where Mary was waiting with a cup of cocoa when Dean got there. “He cheated!”

“Mom said it was okay, even gave me the idea,” said Sam as he hid behind you. Dean turned to face Mary who simply shrugged.

“By the time you two get done fooling around, it’s after noon and then you spend the rest of the day complaining that we’re supposed to open things in the morning,” she said, tossing you a santa hat.

Dean and Sam simply grumbled as they took a spot on the couch behind you. You went to sit next to the still muttering blonde man when his hand found your ass and shoved you forward lightly.

“Uh uh,” he said with a smile. John had made his way over to sit beside Mary, a cup of coffee in one hand as the other snaked it’s way over her shoulders.

“You got the hat. You’re Santa’s little helper this year,” said Sam. You saw both John and Mary make faces at then man behind you.

“Sorry,” said Dean a little sheepishly and you could only imagine the grin he’d had on his face as he’d probably eyed you up and down at your new title. Meanwhile, your own eyes had fallen on the tree you’d decorated about two weeks ago. There was no way for you to explain to any of them, even Dean really, how you couldn’t care less about the boxes that were by your feet. It was the being with a family again that was all you’d really wanted. 

The Winchester’s had more than delivered on that front.

“So…” you said, breaking out of your thoughts when you felt Dean’s gaze on you. “How does this work?” you said, turning around with a smile. The four of them had a silent conversation before they simultaneously turned to you and shrugged. “Weirdos.”

“Your weirdos, kiddo,” said Mary. With that you decided to roll with it, picking up a square box, finding it heavier than expected as you lugged it over to John, placing it beside him on the couch. About five minutes later, you’d finished, failing horribly to hide your own shock and awe at your own plentiful pile of goodies.

“This really is too much,” you said to yourself, nestling in between Dean and Sam, the heat of Dean’s leg pooling into yours from where you touched.

“Sweetheart, the only one who doesn’t think you’re a member of this family is you. Nobody’s treating you special. You remember what mom said when we left for finals?” said Dean in a whisper, his lips brushing against your ear like so many times before. But this wasn’t the dirty teasing in hushed tones, it was the kind of whispering that sent a soft flutter through your heart.

“I remember, I’m family now,” you whispered, so quietly you weren’t sure he heard you. Dean gave no indication that he had as he settled beside you. You parted your lips to say it once more but were interrupted when his soft pink ones occupied yours for the briefest of moments.

“Save that present for later dude,” said Sam from the other side of you as you heard him start to unwrap something.

“Oh, I will,” said Dean with a raise of his eyebrow first to his brother, then you.

“Open up the red striped one first frat boy,” said Mary, shaking her head. Dean went a little wide eyed, certain you’d never used that nickname in front of his parents before. “Y/N and I talk,” she said with a shrug. “And I think it’s adorable.”

“Thank you for that, sweetheart,” said Dean as picked up the fairly small box and tore the wrapping off. You four were already laughing by the time Dean realized what he was holding. “Who did this? Hm?” he said, his gaze finally falling on you.

“All I did was provide the sizing baby,” you said as Mary made a little coughing sound. 

“Merry Christmas, Deanie,” said Mary and John who were almost in tears from laughing so hard. 

“Candy cane flavored condoms. I hate you two, I hate all of you,” said Dean, leaning back against the couch with what you knew was a fake pout. “I liked it better when you didn’t think they liked you.”

“You don’t even want to know what we have planned for your birthday,” chimed in Sam. Dean’s pout turned into a smile as he nodded his head, throwing you a dark glance that you barely had the chance to catch. You were in for it later.

“New Christmas tradition, congratulations Dean,” said John.

“Should I expect anymore surprises?” asked Dean, finally letting it show that he was happy to be the brunt of the joke.

“Of course. But you have to open the rest of your things first,” said John with a wink.

 

By the time you had retreated back to Dean’s room for the night, it was late. John and Mary went to bed hours ago, leaving you with the Winchester boys to have an impromptu snowball fight outside in your pajamas. Afterwords, the three of you crawled up the stairs as you and Dean departed from Sam who had a room at the other end of the hall. By the time you were done with your shower, Dean was already back in your room in nothing more than a pair of flannel pants. 

“Hi,” you said softly as you came in, a towel wrapped around you as your mostly dry hair hung over your showers. Dean seemed to ignore you for a moment when you went to your bag. Or where it was supposed to be.

“Oh, hey,” he said, a shit-eating grin all over his face when you turned around with a huff.

“I’m cold,” you said, even though you found the temperature more than comfortable enough to be naked in the room. 

“Good thing I know exactly how to warm you up,” he said, advancing on you fast. He stopped when he had you so close to the window you felt the chill of it through your back. “You were bad today, little girl,” he said, one of his hands finding the place where you tucked in your towel. 

“But you like candy canes,” you said, letting Dean unfold the towel and open it up like you were the best present he’d seen all day. You didn’t mind that the curtains weren’t drawn. The Winchester home was nestled in the woods, no peering eyes to see in.

“I do love candy canes,” he said, pulling the towel away, seeing your naked body underneath. “But I love fucking you senseless even more.” Dean placed a hand on your collarbone, letting a finger trail slowly down your chest, down you stomach, almost all the way down to your folds when he pressed up tight. His erection was hard, his baggy pants hiding it well as he didn’t move, just let you feel him.

“Dean,” you said, shifting your hips to grind against him. You pouted when he pulled away but found a grin on your face when he dropped his pants. You licked your lips and found Dean laughing.

“Oh, sweetheart, I appreciate the offer but I’m taking a number from our little list tonight,” he said, your pulse shooting through you at the thought.

“Which-”

“Trust me?” he asked.

“Always,” you said. For a moment the dirty talk and need to have your bodies mixed in a tangle of limbs fell away. It was just you and him together.

“Well alright then,” he said, regaining his composure and pulling you over to the bed. “Let’s do this,” he said darkly.

 

“I need you,” you were begging, clawing and reaching at every inch of Dean’s skin you could find. He’d started by flicking his long tongue over your perky nipples, trailing a wet line down to your core as he ravished your clit, lapping up your juices as you came the first time. He gave you no time to recover before his tongue was buried in your heat, leaving slick and rough strokes against your walls, his nose nudging your already sensitive clit as you came again a second time. It was almost too much when he thrust two fingers in, pumping them in time with his assault on your mouth, his face still wet with your juices as they smeared over you. He pushed you hard as you came again. And then he left you alone while he came from a single pump of your hand over him.

“I like to tease,” he said and you groaned against him. You could feel him getting hard beneath you again as your legs wrapped around his waist, arms around his neck. God, all you had to was shift your hips some and you could slide him inside you. To be honest, you weren’t even sure what kink Dean was doing yet. “You’re doing so good for me little girl. I think you’re ready.”

“Ready for what?” you whined into the crook of his neck. You needed something,  _anything_  from him, needed him to touch you the way you needed. Dean swirled a finger around in your still dripping heat, before quickly replacing it with his cock. You were so tight, even if he was so familiar to you now, you almost didn’t register that his finger was teasing your hole. “Dean…”

“If you don’t like it, I wanted you to have some fun first,” he said in a hushed whisper, his finger sliding into you effortlessly as you gripped him tight. But he’d played too long and you needed all of him. You ground back on him hard as he got the message and added another. You had started to feel it but you ground back again.

“More,” you growled, letting yourself demand and not ask. Dean obliged and added a third, a smile falling over you lips as you were full of your Dean. His hips pumped slowly into you as you adjusted to him, preparing you for what was next.

“You want my cock in your ass? Want me to fuck your ass like I fuck this little cunt?” he said, voice laced with roughness. 

“Yes, Daddy,” you whined, desperately trying to fuck yourself on his fingers as well but a strong hand on your lower back preventing you.

“Oh, it’s Daddy tonight? You know Daddy likes to hear you scream,” he said, changing his angle to hit you deeper. You knew that, that Daddy was for nights you wanted to let go completely, for nights when Dean teased your backside like he was doing right now.

“Yes, yes,” you said, feeling yourself get closer to your fourth orgasm of the night. Quickly Dean pulled himself from you, pulling his fingers as well , leaving you a withering mess lying on your stomach. You groaned but heard Dean climb off the bed and then the sound of something snapping. Turning around, you saw Dean pour a generous about of lube into his hand as he stroked his achingly hard cock. “Fuck,” you half-laughed, knowing you’d come right then if he told you to.

“Nice and slow,” he said, crawling back on the bed, settling himself between your legs. His hands spread your ass cheeks as his tip brushed against your hole. You tensed as Dean shushed you. “Relax sweetheart. Tell me if you need me to stop.”

You nodded, letting yourself melt away to him as his tip nestled against you and then you felt him push. Your hands fisted in the sheets as you relished in the delicious burn of him, the stretch of him filling you. Fuck you wished you could see it. Every throb of Dean’s cock felt more desperate, more needy as he slipped his tip in.

“Doing okay?” he asked as you relaxed. 

“Fuck yeah,” you said, not caring at all how whiney and blissed out you sounded. Those fears with Dean vanished a long time ago. Dean took that as a sign to keep going, slowly pushing inch by inch into you as you moaned and praised and cursed into the bed, finally feeling his hips pressed firmly against your ass. 

“Fuck, you feel so…fuck, yell at me later for not doing this sooner,” he said, neither of you moving as you adjusted to one another.

“I need you Daddy,” you said after a few moments, needing him to pound into you more than life itself.

“Anything for you little girl,” he said, carefully pulling out half-way and sliding back in. You went slow, both of you concerned with not hurting the other, until you crossed that line you were waiting to cross, the one where one thrust Dean was careful, the next fucking into you like he owned you.

“Fuck, Dean!” you cried into the bed. 

“It’s Daddy, little girl,” he said, thrusting in harder and not letting up.

“Fuck Daddy. Please, so fucking good,” you praised, his hands on your hips tearing into the flesh harder than ever before. You were totally and completely lost as Dean sent you to a new kind of pleasure you’d never experienced. This was harder, took so much more restraint on his part, so much will power on yours. He wanted you to come just from this, from him pounding into your ass alone.

“Daddy’s close,” he said through gritted teeth, pulling you up and back so you laid on his chest, his cock continuing to pump into you as his hands wrapped around you tightly, holding him against you. “Come on sweetheart, come with Daddy.”

Dean gave one final push as he slammed into you so hard, you would have arched off of him completely had he not been holding you down. You went to cry out as his lips found yours, his moan lodged itself in your throat as you clamped down on him, his cock spilling his cum deep inside you as you rode out your highs. You were in heaven as he pulled out and moaned again into his open and waiting mouth when you felt his cum dribble out of you.

“Merry Christmas,” he said, when you rolled to the side, not caring about the sweaty mess of your bodies or the puddle of your juices mixed with Dean’s cum that was in the sheets.

“Merry Christmas,” you said back, giving him a lazy kiss before the both you passed out, completely and utter fucked.


	16. Chapter 16

**Summary for the Chapter:**

> Dean and reader have a date night…

“You look pretty,” you said, folding your arms across your back as you swung your hips back and forth. Your dress swayed a little with the movement as Dean walked past you, grabbing your wrist as he went, spinning you round until you were dizzy and falling into his chest.

“You look handsome,” he shot back, his lips curled up as he took you in. “And very beautiful like always,” he said, resting his hands on your waist as he slowed, wanting the both of you to remember this night.

“I’ve got a hot date tonight. Wanted to dress up before he tears it all off,” you said, giving his tie a little tug. He raised an eyebrow before walking over to your kitchen counter, lifting up the little pieces of paper you’d each written what kink you wanted to try tonight. You’d left it alone since the holidays but it’d been almost two months and you were ready to try something new again.

Thankfully you two just so happened to pick the same one.

“Just to be clear, when does this go in effect?” he asked, holding up the little slips before tossing them in the trash.

“How about, as soon as we get home and that front door shuts,” you said, Dean’s smile showing how excited he was.

“Lasts until we both…” he said with a cock of his head.

“ _Neither one of us makes a sound until we’ve both come_ ,” you said. “I should know, I wrote it,” you said, holding out your hand for him. His larger and rougher one slid over yours, his free one reaching to hand you your purse and jacket.

“Sweetheart, I’m damn glad you did. I can’t wait for you to lose your own bet,” he said with a chuckle.

“Frat Boy’s got a big mouth. Let’s see if he can keep it shut tonight,” you said, dropping his hand for only a second as you both put on your winter coats.

“Y/N?” asked Dean, your eyes traveling up to see his smiling eyes. “Happy Valentine’s day, sweetheart.”

“Happy Valentine’s day, Dean.”

 

Dean could really be a hopeless romantic when he wanted. When you pulled up in Baby to the nicest restaurant in town, you couldn’t help but shake your head.

“How long have you been planning this? This place is notorious for the months long reservation list,” you said, staring at him with wide eyes as he gave the tiniest of shrugs.

“A while. Keeping it a secret from you was harder,” he said, climbing out and handing his keys to a waiting valet. Dean opened your door for you, nearly lifting you off the ground so you’d avoid a pile of fresh snow as you stepped out.

“Let’s hope it lives up to the hype,” you said.

Three hours later as Dean opened your door, you were still in debate over whether that meal was as good as sex with Dean Winchester. Dean had moaned after one bite, something that would rival the sounds you thought only pie could pull from him. That was of course until he had pie for dessert. You thought the man might come then and there.

“Can we make another reservation?” he asked, barely two steps out the door. 

“How about one for when fall semester starts back up?” you asked, seeing him already putting it on his to do list. He slipped around to the other side of Baby, taking you in for the millionth time that night but this time a little different. The way his head tilted, his green eyes slowly danced from one spot to another, his breathing relaxed. You smiled as he memorized this moment. 

He gave a coy smile as he realized you’d let him take his time, had caught on to him. He rubbed the back of his head before sliding into Baby, the blush on your cheeks hot as fire. Even in the dim light of the car as you headed for home, Dean was biting his bottom lip, trying unsuccessfully to keep the smile off his face. He was a hopeless romantic after all.

 

“I love you,” said Dean when he turned off the engine outside your house. He brushed a strand of hair behind your ear, his finger tickling the sensitive flesh there as you squirmed into him.

“I love you too,” you said, reaching your hands for his exposed ribs, the man always ticklish under your soft touch. For a moment that’s all you were, two people in love, having a tickle fight in the front seat, laughter squealing its way from you, deep rumbles of it booming from his chest. When you’d decided your sides were about to burst, you pulled back, Dean doing the same. With panting breaths and silly grins, you both nodded and climbed from the car.

“Not a peep from you little girl or I get to punish you later,” Dean said when your hand was on the front door. You widened your eyes.

“Oh, so were adding rules now? I’ve got one of my own then,” you said, watching him lick his lips absentmindedly.

“Go on,” he said, his pupils growing dark right before your very own.

“If you break, I get you,” you said. You could tell he was confused. “Oh, I know I already got you, Frat Boy. This…I get #1 of yours on that list,” you said, watching his sharp gulp of air.

“I’ll lose on purpose then,” he said. You were impressed with how much he wanted that one. But you knew exactly when you wanted to test it out and that wouldn’t be for quite some time.

“Work together then tonight. I’d love to see you lose it but I’d love to see me stop that from happening even more,” you said, Dean’s hand lightly shoving your door open. You both took a step inside.

“Love you,” you said in unison, Dean’s hand pulling the door shut, starting the game.

If there was one thing even Dean Winchester couldn’t make sexy, it was taking off a winter coat but boy did he try. You wanted to laugh and almost did when Dean’s finger found your lips, silently shushing you. His eyes gave you a look.

_Don’t break that easy, sweetheart._

_You look ridiculous._

_You look hot._

You were shaking your head as you smirked. This was how it had to go, conversations with your looks alone. Dean threw you another one when you were in only your dress.

_I want to take that off._

At least that’s what you guessed as he stalked his way over to you. Your hands were on his tie, pulling him down into a gentle kiss as you removed the silky material from his neck. Large hands found your bare shoulders, rubbing down your back until they found the zipper of your dress. Dean’s tongue slipped into your mouth, curling around yours, the taste of him everything you could want. You fumbled with the buttons of his shirt as he pushed the strap of your dress off one shoulder, waiting until you’d untucked his shirt to give the other the same treatment.

You slid your hands across his stomach and up his chest, his lips against yours pulling up into a smile. He swirled around the inside of your mouth as though he’d never kissed you before, taking his time as you pulled his belt through the loops. As your dress finally fell away, Dean moved his lips from yours and moved them, about to tell you he loved you but yours found his instead. You brought a hand up to the back of his head, pulling him closer.

He nodded in understanding, shifting his shoulders so his jacket and shirt fell away, leaving him in only his pants. His hands grabbed hold of your waist, giving a small grip on it as his thumbs ran circles into your ribs. You wanted to explore his broad shoulders with your fingers, trace over the way the muscles moved at the smallest of touches. Dean showed no urgency tonight, your romantic wanting to show you all the love he had for you on your first valentine’s together.

Dean’s hands found their way to your arms, rubbing up and down as he pulled you against his chest. His lips kissed along your jaw, dipped along your neck but he wasn’t marking you up tonight. Hands under your thighs lifted you off the ground, your legs wrapping around him easily as he carried you into your bedroom, opening and closing the door without dropping you an inch.

It was much warmer in here as you smiled, nudging his cheek so he’d see it. 

_Thanks for turning on the heat._

_You don’t have to thank me for that._

He looked on with hazy eyes, high on you, holding you close as he brought you over to the bed. You unhooked your ankles and dropped them to the ground, finally undoing his zipper, feeling him hard under the material. With one easy tug, his pants fell off, his long legs kicking them to the side. Even when Dean liked to go slow, he hardly ever left you in your bra and underwear by the time your back was hitting the mattress.

But tonight, his strong arms wrapped around your body as they lowered you down, neither of you able to see the other fully. He continued his easy kiss, the weight of him so close to you making you catch your breath, pressing your chest up into his. At some point your hips were lifting up, grazing against him, not grinding yet, but asking for more. 

He rolled, bringing you on top of him as he sat the both of you up, your body straddling his lap. Finally, his hand found the clasp of your bra, sliding the straps off your shoulders, rubbing the muscles where they’d spent the day digging into your skin. You nearly let out a grateful moan, this man was such a godsend. You bit your lip to keep it down, the sound of the bra being tossed to the side reminding you to focus.

With another shared look, you both lifted your hips, letting the other pull off your bottoms, Dean feeling the soak of yours, you feeling the stain of precum on his. When they were gone, you settled back onto his lap, guiding his hard cock through your folds as he stretched you, filling you in a way that had you dropping your head on his shoulder. 

One of his hands found your lower back, pressing you further onto his cock, your mouth on his shoulder as you breathed deep. He slid it up your back as his head nuzzled yours. When you lifted it, he was smiling, leaning in as you did the same, swollen lips meeting again, fitting together effortlessly. Your hands curled under his arms, one hand against his upper back, the other, against the back of his neck, fingers dipping into his blonde hair that made your heart flutter every time you saw it.

Dean’s arms moved to hold you in the same way, one of his running against the back of your head, playing in your hair. He didn’t pull, only rubbed his fingers into your scalp soothingly, his other arm wrapped across your back, holding your body against his. Then without realizing, you started moving your hips together.

Dean pushed forward as you rocked back, pressing him deep in you, letting him feel the drag against your walls. When you pushed forward, Dean pulled back, his cock throbbing in you making him suck deep for air, lips locked on yours. Sitting upright like you were, Dean didn’t have the best angle for deep, powerful thrusts you would have squirmed at, you didn’t have it for hard snaps of your hips that made Dean whine.

You had a slow grind, a smooth rocking back and forth, pushing and pulling back on one another. All the while, your hands tickled the others skin, held each other close, let your never ending kiss keep you quiet. Dean was slick with sweat as you felt the beads of it run all across your body, somehow the mix of it proof of the lengths you were willing to go tonight.

You never tired, the motion too easy for you to need to stop anytime soon, even when you saw through half-hooded eyes that you’d been like this for longer than most of your whole sessions. It was such a slow build, you were a little terrified of what would happen when it finally came. You saw it in Dean’s eyes too, positive he felt that pressure inside so much more than you’d ever felt before. 

You were settled in your rhythm when Dean was kissing you harder, his teeth biting your bottom lip. He was close and holding off for you as best he could. You scooted up on his lap a little and felt him hit you deeper. You dug your hand into his back, his lips crushing yours as he inhaled harder than you’d ever heard in your life. You rocked a few more times and felt yourself hit that same spot, your body as tense as his was. You opened your eyes as best you could to find his half-open, half lost to pleasure like yours. You were both ready.

You kept going with your pace but relaxed, Dean doing the same as you felt your bodies hit that peak. It grew and grew, your walls clamping down on Dean so hard, you could feel his cum hit you with more force than ever before, your arms holding onto him shakily. You didn’t know how long your orgasm lasted but you knew it was surely the longest of Dean’s life, his mouth opening against yours as you felt him moan into yours, you doing the same, the sound not even audible from the slow meeting of skin on skin that was in tune with your heartbeat.

By the time you’d come down, Dean had softened inside you, his arms still wrapped so tightly behind you, you weren’t sure he’d ever let you go. Your finger brushed against his cheek, grazing over his freckles as he opened his eyes, lips finally breaking from you.

“I love you, Y/N,” he said, the sound of his voice something you realized you’d never want to live without.

“I love you, Dean,” you said, seeing a similar reaction run across his face. Carefully, he helped slide you off of him but kept you on his lap, his hand running through your hair and over your back.

“That was good,” he said as you nodded in agreement. When you’d written that down, you’d always imagined it would be rough, Dean clamping his hand over your mouth as he pounded into you, you holding one over his to keep him from crying out your name. Someday you’d try that, but tonight…you wanted to be a hopeless romantic right along with Dean.

“Happy Valentine’s day,” you said, smiling so wide it hurt.

“Happy Valentine’s day, sweetheart,” he said back, the same smile on his.


	17. Chapter 17

**Summary for the Chapter:**

> Dean and reader have the frat to themselves and decide to have some fun…

“Dean…” you sang out, wandering around the second floor of the frat house in a pair of pajama shorts and one of Dean’s tees. “Frat Boy…”

Unfortunately, he wasn’t taking the bait. You were going to have to find him on your own. You skipped down the stairs, deciding to begin your search there. He wasn’t in the living room or the rec room, nowhere to be found in the kitchen. You checked the laundry and even their study room which was wiped clean now that finals weeks had finished up and everyone was gone.

Which was exactly why you and Dean had the whole frat to yourselves tonight, Sam staying a friend’s because he wanted to be nowhere near the two of you once you got going properly. 

“Dean, I’ve been a bad little girl…” you said loud but still smooth, enough that his cock would twitch at the mere sound of those words. 

“I can see that,” said a voice behind you, making you jump a little.

“How did you-” you said turning around to see Dean in front of you, biting back a laugh.

“You got something to say miss?” said Dean, crossing his arms over his chest, showing off his muscular arms.

“Of course not officer,” you said, unable to keep down your giggle. “Baby you look so-”

“Do you live at this residence miss?” said Dean, putting his hands on his hips. Oh boy, was he getting into it.

“No, but my boyfriend does,” you said, giving him a smirk. When Dean’s list had included role play, you figured he’d want to dress you up as a sexy nurse. So when he asked if the two of you could do it tonight, you were down but never suspected  _he_  was the one that wanted to play dress up. You’d never suspected that it would make you as turned on as you were.

Dean Winchester in uniform was  _fucking hot_.

“Is he here to verify that information?” said Dean, giving you a smirk of his own.

“No but I can call-”

“Miss, I’m going to have to charge you with breaking and entering. Turn around and place your hands against the wall,” he said, nodding towards the one just beside you. You only stood your ground, lips curling up into a dark smile. Dean had been sweet as of late, something that you loved to be with him. 

But tonight you and he both wanted you pinned to a wall and screaming his name as he fucked you so hard you’d feel it for a week.

“Miss, I am authorized to use force if necessary,” he said, taking a step towards you as you shrugged. He gave you a long glare before one of his large hands reached out and found the middle of your back, turning and pushing you all at the same time so you came face to face with the wall.

“Officer, I’m sure we can reach some sort of understanding,” you said, turning your head, Dean’s hands sliding yours up the wall, pressing into them roughly.

“There are reports of a dangerous criminal in this area, goes by Y/N. You wouldn’t happen to know of her, would you?” said Dean in your ear, his chest pressed up against your back as he nudged your legs open with his thigh.

“No, officer, never heard the name,” you said, soaking in the nervous excitement as Dean ran has hands down your arms slowly, squeezing and touching as he went.

“I’ll have to search you before I take you in,” he said, practically growling, the rumble in his voice sending sparks through you. “Y/N.”

“But officer-”

“You’re wanted. Bad girls like you need to be punished, Y/N,” he said, rough hands sliding down your torso, stopping when they reached under your shirt and crawling back up again. He took his time once his hands found your breasts, no bra in the way as he started kneading the tender flesh.

“Dean,” you said, trying to arch into his touch as best you could.

“Officer Winchester to you, sweetheart,” he said, his fingers finding your nipples and rolling the buds with some force. You whined when he finally dropped his hands away, your body more than ready to turn around and pounce on him. But he was in control tonight and you had take whatever he was giving. Unless…

“Officer, I really think I could do something for you,” you said, grinding back against him hard, surprising him as you ducked out of arms reach. You thought you had a chance, would make him work for it a little more, when two strong hands grabbed your arms and pulled you back. Fuck, you forgot how strong he was as you squirmed beneath him, no match at all.

“That’s it, I’m restraining you,” he said, facing you towards the wall and momentarily letting go to pull something from his belt. His hands were on your wrists, tying them with one of your silk scarves as you struggled a little, just so he could feel it. You gave a good tug on it when he’d finished and almost laughed. He’d gotten good at making sure you weren’t getting out unless he let you.

“I’ve got information I’d be willing to share if you help a girl out,” you said, Dean’s hands already on your hips and sliding the shorts off your body with ease.

“I should add trying to seduce an officer of the law to your list of offenses,” he said, fingers dancing down your hips, hands diving close to your core before running along your thighs. “I’ll make a deal.”

“I’m listening,” you said, grinding against Dean’s cock, hard in his pants. 

“A bad girl like you needs to be punished. I’ll fuck you until I’m good and done and in exchange, I’ll forget I saw you here,” he said, fingers moving to play with your folds.

“Yes, Officer Winchester,” you moaned. Dean rewarded you by thrusting a finger in, pumping fast in and out. He pulled your earlobe out between his teeth as he added two more fingers without warning. You bit down a whimper as Dean’s lips sucked and nipped just under your jaw.

“Don’t do that,” he whispered against you. “I want to hear you.” Glancing down, you had the perfect angle to watch Dean’s fingers disappear inside you, over and over again. Your walls were already clenching around him as you felt the roughness of his skin penetrate deep inside, curling at the last moment to hit your g-spot.

“Fuck,” you groaned out, long and low as your legs began to shake. Dean’s free arm wrapped around your waist, pinning you to him as he shifted his hand, the new angle hitting you with perfection. “Dean,” you whined, hands behind you fisting in his shirt.

“Go ahead. Come. Now,” he ordered, voice too rough, breath too hot on your neck for you to dare disobey. Dean never let up, kept up his harsh pace as you moaned and grunted out his name, not stopping until his arm was the only thing keeping you standing. When he pulled his fingers from you, he brought them to your face. You opened your mouth but could only watch as he lowered his head next to yours and sucked them clean. “Delicious.”

“Officer,” you said, leaning your head against his for a moment before he suddenly released you, spinning you around so your back hit the wall. Dean dropped to his knees so fast you nearly came again.

“We’re just getting started,” he said with a devilish smile, his hands cupping your ass as he dove his face against you.

The sound you made was obscene but that only turned Dean on more. His tongue was sucking and lapping at your neglected clit, giving it the proper attention it so desperately needed. Your hips bucked forward, strong hands capturing them to hold you steady.

“Dean,” you whined, wanting nothing more than to be able to run your fingers through his hair, tug his mouth closer against you. But you could only strain against the scarf, the feeling of being helpless making your heart race. You watched as one of Dean’s hands trailed up under your shirt, under his shirt, kneading your breast, a primal moan escaping you. “Please baby.”

Dean hummed as his scruff tickled and scratched your sensitive skin, his lips in a smile as he took your swollen clit in his mouth and sucked hard and long. A shockwave shook through you as you suddenly came, your head falling against the wall as you shouted his name. Again, Dean worked you through your orgasm until you were a trembling mess.

“Better but I want you to scream,” he said, standing as you tried to catch your breath, not daring to move as your legs would surely give out. Hungrily you took in Dean as he shed his shirt, undid his belt, and dropped his pants and boxers before stepping out of them. With no fanfare at all, Dean’s hands were on your shoulders, pressing you up against the wall, his cock sliding into you in one fast motion.

“Fuck!” you yelled, hands clenched into fists, toes curling as you stood up on them, every cell in your body charged with dangerous fire. Dean’s cock was pulsing with need, ready to explode as he pulled out and thrust in hard. Every time you arched your back, it only made him hit you deeper, only made you cry out his name as his lips captured yours, stealing every moan you had to offer.

Dean grew erratic as his rhythm faltered, pumping so hard your legs had wrapped around his waist so you could feel every glorious inch of him. You could feel his hip bones clash against yours, the force of it sure to bruise the both of you. His head leaned in, forehead resting on yours as you could feel him swell and come inside you.

“Dean!” you screamed, so loud the whole neighborhood must have heard. Dean rutted against you as he filled you to the brim, your mouth falling to bite against his muscular shoulder as your body quaked through another orgasm. When Dean had finally grown soft inside you, he pulled out, a trail of his cum leaking down your leg. Dean thrust two fingers inside you, making you moan, curling them before pulling out and bringing them to your lips. You opened your mouth and sucked on them, savoring his taste as you licked him clean.

“I think you’ve learned your lesson,” he said, turning you around once you’d found your footing. “Nothing to report here.” His hands made quick work of untying you, his hands rubbing your shoulders soothingly for a moment before stepping back. 

But then Dean turned his back to you and it was suddenly apparent to you that he’d handed you the scarf. You smiled as you walked up behind him, lightly taking one of his wrists in your hands.

“Something I can help you with miss?” he asked, not turning around. You knew he wasn’t going to give you long as you tied his hands behind his back, barely finishing before he was tugging on the scarf. “What the hell do you think you’re doing?” he asked, his breath already catching in his throat.

“You can’t change a bad girl, Officer Winchester,” you said, whispering in his ear as he took his turn to shudder. You placed a hand on his large bicep and pulled him down to the ground so he lay on his back, arms behind him as he stared up at you. “You shouldn’t have released me. I am a dangerous criminal after all,” you said, running a hand over his cheek, down his throat and over his heaving chest.

“Let me go,” he growled as you straddled his lap, leaning over to stare down at him. He squirmed a little but soon shut his eyes in defeat. When he finally opened them again, he saw you’d put on the top part of his uniform, a happy sigh escaping him.

“But you’re so pretty tied up for me,” you mumbled against his lips, rough and low. “Now Officer Winchester, how should I punish you?” you asked, scooting back to line yourself up with him. You sank down on his growing member, Dean moaning as you took him to the hilt.

“Y/N,” he said through gritted teeth. “When I get out of here, you are in so much trouble.” You only smiled as you ground your hips down, his cock twitching and jumping inside you as you could tell he was almost hard again.

“I better not let you out then,” you said, bracing your hands on his chest as you raised yourself up and slammed down.  Dean was fighting back the desperate sounds that wanted to leave his pink lips until you sat up straight.

“Fucking shit, Y/N,” he breathed out, his hips trying to shift up under you. 

“No no little boy,” you said, your hands pressing down hard, stilling him as you continued to pick up your pace, Dean ready and throbbing inside you again.

“Please,” grunted Dean and you slowed down, giving him only tiny rolls of your hips. “Oh come on,” he said.

“You going to scream for me?” you cooed in his ear, kissing along his cheek. He seemed to debate it as you pulled his bottom lip out between your teeth. 

“Yes,” he said, swallowing thickly.

“Yes, what?” you said, running your hands in his hair as you offered only the small movement.

“Want you to make me scream,” he said, voice whiney and desperate.

“Only because you asked so nicely, Officer Winchester,” you said, leaning back as you rode him hard, the sound of your slick, sweat covered skin gliding against Dean’s filling the air. After a few minutes, Dean was whining and whimpering without shame, even though you knew he was no longer afraid to be that way with you. 

“Y/N,” he whispered, as he looked on with pleading eyes. You were just as close as him, your hips snapping into action as you went hard, grinding into him even as you felt Dean swell up and come again, your name falling from his lips so loud now you  _knew_  the whole neighborhood had heard. You worked through to your fourth orgasm of the night, this one no less powerful as you clawed at his skin.

“So officer, did you enjoy that?” you said, finally rolling off of him, running a hand through Dean’s hair.

“That was more fun than I thought,” said Dean, eyes raking over you as he came down from his high. “You in that uniform…” he said, biting his bottom lip.

“That’s Officer Winchester to you, sweetheart,” you said, imitating Dean, watching as he laughed, his chest rumbling as it made one of your favorite sounds on earth. You helped him sit up and rubbed his shoulders but Dean groaned again after a few moments.

“Fuck, you’re not done with me, are you?” he said, turning his head over his shoulder. You giggled as you stood up, shedding the shirt and shrugging innocently.

“Me? I’m going up to bed, Dean. Whatever you decide to do when you get up there is entirely your decision,” you said, crossing your arms behind your back as you took a step backwards.

“I’d go hide sweetheart because when I get out of here, you are in for it,” he said with a smirk, already shifting so he could stand. 

“Guess you’ll just have to catch me then,” you said, heading up the stairs by the time Dean got to his feet.

 

You hadn’t expected Dean to get out and find you  _that_ quick. Fuck, you’d barely made it the third floor by the time you heard him shout from downstairs that he’d cut himself free. You made a beeline for Dean’s room without thinking, and dashed behind the door. About fifteen seconds later, Dean entered and slammed the door without looking.

“I know you’re in here,” he said cockily, moving towards his closet. Spinning on your heels, you put a hand on the door but heard a cough behind you. “Get on the bed,” he said, his body close to yours. 

“You know, we’re going to the cabin tomorrow, we should probably get some sleep,” you said, looking up as Dean towered over you.

“Get on the bed,” he said again, a little more force this time. You did as told, laying on your back and shutting your eyes. Of all the things you were expecting, Dean cuddling up against you and throwing a sheet over the two you was not one of them.

“You tricked me,” you said, turning so you could face him. His face was glowing as he smiled, his arm taking its natural place over your waist as it held you protectively.

“I never said  _what_  you were in for. Such a dirty mind,” he said, nuzzling his cheek against yours, pulling a giggle from you.

“Love you,” you said, staring into his bright green eyes.

“Love you too,” he murmured, kissing you goodnight. “Get some sleep, we got to get up early.”

“Night, Dean,” you said, resting your head close to his.

“Good night sweetheart,” he said, his content face the last sight you saw before falling into a peaceful sleep.


	18. Chapter 18

**Summary for the Chapter:**

> Reader has a relaxing summer day with the Winchesters…

Dean’s hand was crawling dangerously high up your bare thigh, rubbing a little too gingerly for a simple make out session.

“Dean,” you whispered in his ear, his hair still damp from your recent morning swim in the lake. “Sam will be back any minute.”

“We better be fast then,” said Dean, his lips latching onto that sensitive spot on your jaw that made you whine as a hand danced over the drawstring of your bikini bottoms.

“Frat Boy,” you growled, pressing a hand up to his chest, pushing him back. Dean pulled away, giving you a pout. It was the middle of summer, Dean’s skin a little more tan than you were used to, his freckles standing out more than was fair. In a flash, he shifted from scolded boy to feverish man, practically tackling you to the ground as your back hit the warm grass beneath you.

“Can I at least kiss you?” he asked, already feeling your hand in the back of his hair pull him down. You smiled as his lips found yours, Dean’s body shaking through a chuckle. “I’ll take that as a yes,” he mumbled against you, his soft pink flesh on yours a sweet mix of fresh watermelon and a taste of alcohol.

“I’m home guys,” said Sam, walking past you as you lay on the grass, the splash of water telling you he’d gotten in the water. You heard him laughing and couldn’t help but wonder why. It wasn’t like he hadn’t seen you and Dean kissing, making out, a thousand times over the past two months. “Three…two…one…”

“Sam!” you and Dean shouted in unison as you felt a bucket of lake water be dumped on you.

“I let you have alone time _all_ morning. Come on, let’s take the kayaks out,” said Sam. “Pitch the tent tonight, make out later. I’m sure Y/N can only handle so much of your sweaty body on her.”

You couldn’t help but laugh and shrug in agreement. Dean eyed you both mischievously. You quickly crawled out from under him and ran behind Sam, stopping Dean in his tracks.

“You’re gonna get it later, Sammy,” said Dean, pointing a finger at him. “And you,” he said, turning to give you your turn, “You’re  _really_ gonna get it.”

“We’re so scared,” you and Sam said in unison, faking fear as Dean put his hands on his hips.

“Shudyup,” he said, squinting before giving a wide smile. “Lead the way Sam,” said Dean, waving off towards where the kayaks were kept. You followed Sam down the path as Dean caught up to you, one of his hands brushing up against yours as he walked by your side. Eventually you took his in yours and heard him laugh. “Can’t keep your hands off me, can you woman?”

“Yes, that must be it,” you said, giving a squeeze of your hand as you turned to face him. Dean looked happy, content in a way that he always seemed to be now. Without classes, he had all the time in the world to just be with his two favorite people, you and Sam. You just hoped he knew you felt exactly the same.

“For the shortie,” said Sam when you and Dean got to the supply shed. Sam pulled out Dean’s lifejacket and tossed it to him, an amused expression crossing Sam’s face and a pout on Dean’s. “For the clinically insane,” said Sam tossing you your jacket, Dean’s old one.

“At least I have a girlfriend,” said Dean, putting his arms through the vest and dragging his kayak and Mary’s deep red one out for you.

“I still have no idea what you see in him,” said Sam with a teasing smile. He knew  _exactly_  what you saw in Dean. You two talked, almost as much as you and Dean did. But you were his pseudo little sister now and it was his job to make just as much fun of you as he did Dean according to him.

“He’s got a big…ya know,” you said, raising your eyebrows with a cocky smile.

“Information I don’t need to know, Y/N,” said Sam, laughing through his groan. He pulled his kayak down as both boys put on their vests, Dean carefully watching as you did your own. He came over and checked it, tugging on it like always, giving Sam’s a glance over but not going as far as physically testing it. When he was satisfied he gave you and Sam a silently nod, watching as the two of you rolled your eyes but let him call the shots. 

Dean pushed you out after you were in, he and Sam soon following suit as you paddled out to the middle of the secluded lake, Dean always making sure he had the two of you in his sights. You might have been adults but he was also Dean Winchester, overly protective of you and Sam for about as long as you’d known him.

You let yourselves drift in the current, lounging back as best you could as you took in the warm summer day. There was a slight breeze like always out on the water but it was refreshing as the sun beat down, the trees on the water’s edge swaying in the movement. Dean started humming the chorus of one of his favorite rock songs and before you knew it, had lulled you into a light sleep.

“Aah!” you shrieked as you felt cold water being splashed on you from either side, stirring you awake. Dean and Sam were laughing hysterically as Dean kept a steady hand on the kayak so it didn’t flip.

“It’s been about an hour sweetheart. We’re getting hungry and then were thinking a swim to cool off,” said Dean, patting the top of your head. You yawned and sat up more, nodding in agreement as you began to paddle back in. 

When everything was once again packed away, Dean gave you a piggyback ride to the house, the two brothers  having a meaningless conversation on the way back about who would make lunch. You kept quiet as Dean finally dropped you to your feet at the back door, opening it as you skirted in past them. 

“Outside boys, I got this,” you said, moving to the fridge and tossing a few things you’d made that morning into the floating cooler the Winchesters had. “Meet you on the diving dock.”

Sam and Dean did as told and left without a word as you grabbed the other one and filled it with drinks. They were a little heavy but you managed on your own, seeing the boys climb up on the dock as you shut the back door. Once the coolers were in the water you simply pushed them over, each of them taking one as Dean lifted you up to sit beside him.

“You’re amazing,” said Dean, pulling out the sandwich labeled for him and finding it was his favorite kind. Sam had a similar smiling expression on his face as he bit into his. You let your feet dip in the water as you ate lunch with your happy little family. 

Sam finished first and soon was lazily playing in the water, you following quickly after. Dean stayed on the dock, fumbling with the radio that had been left out, pulling his knees into his chest. You propped yourself up on your elbows as you waited for him, a goofy smile on your face as you spotted the bottom of his feet.

On the sole of his right foot was a faded little scar, one that you found yourself reaching out and touching, making Dean jump some.

“Sorry,” you said, turning the motion from ticklish to a smooth rubbing. Dean smiled wide.

“I love that scar,” he said. “It’s from that night-”

“The night I called you and you came to save me,” you said, your eyes gazing up to find his looking down softly.

“I knew that night,” he said, eyes crinkling from where he was ginning so hard.

“Knew what?” you said with a coy smile, tilting your head. Dean shook his in return as he bit his bottom lip.

“You’re going to make me say it?” he said, a light blush falling over his cheeks. You loved that you could still make him blush.

“Frat Boy, I honestly have _no_  idea what you’re talking about,” you said, a small heat running over your own face. You both smiled, Dean savoring the moment as you took your turn to tease him about it like he often did to you. It was the night both your hearts knew before your heads that you were supposed to be something more.

“You’re being a little trouble maker today,” he said, scooting forward so he could hold your hand. “Just giving me reasons to do things to you later.”

“There’s two things left we haven’t done yet,” you said, one of his fingers running patterns into the back of your hand.

“I have an idea which one. I trust myself enough to do it now,” he said, telling you without saying exactly what he was planning for tonight.

“I’ve always trusted you,” you said, letting your words linger in the air. “Tonight then, we’ll do it in the tent after Sam heads inside?”

“Deal,” said Dean, letting you tug on him to pull him into the water. He slipped in beside you, giving a small splash as you drifted away, finding you return one back, Sam coming over to join in and starting off your afternoon together.

 

“I’m heading to bed guys. G’night,” said Sam as he stretched and gave a wave before entering the house. You and Dean stayed by the dwindling fire, staring up at the star-filled night sky for a long time, not saying anything at all. Eventually your mind began to wander and you wondered if Dean had forgotten about his promise.

“Want to do this?” said Dean with a sheepish smile. You gave one back but nodded. You sat upright and crawled into the nearby tent, you and Dean shedding your clothes and kicking them out of the way until it was just the two of you in the dim light given off by the fire.

“You still okay with this?” you asked, running a hand down Dean’s chest, trying to ease any nerves he still had. He nodded in reassurance before inhaling deeply.

“ _Breath play on me_ ,” said Dean. “You still want me to do this sweetheart?” he asked, trailing a hand up to ghost over your neck. You gave a small gulp but knew you still wanted to try it.

“Yeah, I do,” you said, unfolding your legs so you could stretch out on your back. Dean lowered himself over you, caging your body in as he peppered you mouth and neck with soft kisses.

“Tell me what you’ll do if you need me to stop,” said Dean, an edge in his voice. He was still nervous like you and you understood why. Dean could never live with himself if he accidentally hurt you. 

“I’ll tap your nose three times,” you said, Dean stopping with the foreplay to lean back and laugh.

“My nose?” he asked, with a smirk and dark eyes. “Why not my wrist?”

“Because I’m going to be digging into it with my hands probably and I want things to be very clear for both of us if I need you stop. This is supposed to be hot not scary, Dean,” you said, a hand in the back of his hair pulling his mouth close to yours.

“Nose three times, got it,” he said, his voice smooth and more relaxed. With that he started to go to work.

About fifteen minutes later you were lifting your hips up of their own according, asking Dean to move faster but finding he wasn’t giving you anything more.

“Fuck, Dean, I’m close,” you growled, needing him to pound into you like your life depended on it. 

“Good, sweetheart,” he said, his right hand moving from the side of your head to rest on your throat. You didn’t slow your movements any as his fingers felt your pulse underneath. “Tell me again.”

“Nose, three taps,” you said, seeing his green eyes ready themselves. Dean’s pace increased some as he simply let you feel the weight of him on you, not doing anything yet. You brought your hand to his wrist and squeezed, telling him it was okay. 

Dean gave a little pressure, enough that you felt it but not all the way quite yet. He grew more confident as he slammed his hips against yours, slowly applying more force until he paused and relaxed, letting you get in one last big breath before he squeezed hard. You went to take another, to ask him for more but found you couldn’t, not a sound escaping your lips.

Dean’s next thrust into you made your mind jump, sent the heavy build up in your core through every fiber of your being, your head swirling. Muscles you didn’t know existed were tensing and flexing, your head getting lost in the pure pleasure you were experiencing.

“Fuck you’re so good like this,” groaned Dean, feeling you clamp down on him as hard as when you came, even if you weren’t there yet. Your fingers were clinging into his skin as your pulse raced through your ears, thumping as you got distracted by it.

Then Dean was letting go and cool air rushed into your lungs, your body sharp and every touch intensified as he snapped his hips, his cock rutting in deep.

“Dean,” you said, desperate and begging, your hand squeezing his wrist, wanting more. 

“I got you sweetheart,” he said, making sure you caught some of your breath back before his hand grew tight on your neck once more, no fear this time. The second you found yourself unable to shout out his name, you lost the logical part of yourself. Your legs started shifting under him, your hands clawing at his arms, breaking the skin as Dean went hard and fast, hitting you so good you would have screamed if you could.

Dean grunted as he forced his eyes to stay open and watch yours, noting how you weren’t telling him it was too much. With one final thrust, Dean hit that sweet spot and you were coming so hard your orgasm sent Dean into his, the flashing and thumping of your head so much and so good until Dean’s hand fell away.

“Dean!” you shouted so loud, your orgasm suddenly so pointed as you sucked in air, Dean’s hand running soothingly over your neck. You were shaking as you struggled to come down, everything so sensitive, even as Dean carefully pulled himself from you.

“Y/N? Sweetheart?” he cooed into your ear as you found you were laying against him now, head on his chest. You tickled his stomach for a second, using up the last of your energy and gave him a smile. “How was that for you?”

“Good, it was good. Thank you for that,” you mumbled. “How about you?”

“It was good for me too,” he said, as you realized for the first time how Dean was breathing in long heavy spurts as well. “Maybe someday I can have a turn.”

“I’d love to,” you said, failing at fighting off the sleep your body wanted. 

“Sleep sweetheart,” Dean whispered, pulling the sleeping bag up over the two of you. “I love you.”

“I love you too, Dean,” you said, falling asleep faster than ever had in your life that night.


	19. Chapter 19

**Summary for the Chapter:**

> Dean and reader recall the night they met…

“Dean?” you asked as you skipped down the steps to find Dean in the frat’s living room. He hummed in response as he shut his computer before you could see what was on it. “What are you doing?”

“Nothing,” he said with that smirk that told you he was planning something. “Do you know what day it is?”

“Saturday?” you said, ruffling his hair as you walked past and into the kitchen. Cas was on his way out and told you good night with a wink before you heard the front door open and shut not long after. “What are you up to?”

“Is it  _just_  Saturday?” said Dean as he leaned against the doorframe, watching you pull a drink out of the fridge. You squinted in confusion with your back to him. Then a long and low whistle fell from Dean’s perfect lips and it clicked.

“Still enjoying the view I see,” you said, standing up with some cockiness and spinning on your heels. “You got something planned for tonight, Frat Boy?” you said, brushing past him and into the rec room. You sat down your drink and found Dean picking it up as you grabbed a pool cue.

“Nah, I’m a good boy now,” he said with a cock of his head. “None of that rough and gruff stuff. I’m a taken man,” he said, grabbing a cue as you set up a game for the two of you.

“Stop teasing,” you said, putting a hand on your hip and raising an eyebrow. Dean chuckled as you stood your ground. “Mr. I think of everything has nothing in mind for the night we met?”

“How about you just forfeit and you can find out,” he said, grabbing your cues and tossing them on the table. You held out a hand and found his fall over yours, guiding you up to his room. You were hit with a rush of excitement like you were the night you met but this was different. After a year you still got butterflies from him, still blushed furiously from his simple touches.

Dean’s room was a little cold as you entered, his hand dropping away to turn on the heat. It was rare that you spent the night here anymore with Dean having moved into your apartment at the start of the semester. Only if you were tired did you sleep in his old bed. He didn’t have much there, most of his things at your shared place apart from a few articles of clothing.

As you glanced around and noticed how Dean and you didn’t have separate spaces anymore, his lips found themselves brushed up against your ear.

“You remember that night?” he whispered, hands resting on your hips. You nodded into him as your hands reached behind you to undo his belt. “Do you remember what we did?”

“Yes,” you said, turning around so he could see the glow on your face. You thought maybe you were in for a repeat performance tonight but Dean’s face said otherwise. He didn’t stop you from pulling his pants down or lifting his shirt over his head, didn’t chide you when you removed your own so it was just the two of you in underwear.

“I was thinking…” he said, taking a step forwards, walking you back until your knees were touching the edge of the bed.

“Don’t hurt yourself babe,” you said, teasing him back. Dean curled up his lips into something dark but loving.

“The one we haven’t done yet,” said Dean and you instantly knew he was talking about the kinks. There was only the one left, the one Dean wrote first but had been patient, nearly a whole year of waiting for it.

“ _Break your record_ ,” you said, stepping to the side and turning him so his knees were hitting the back of the bed. “You want me to do that little boy?” you said, taking a step forward and watching him fall back on the bed. “Make you come four times tonight?”

Dean swallowed thickly as he nodded. You’d pushed him to three before and thought he’d broken he’d come so undone. But you weren’t about to tell him no.

“Take off the rest of my clothes,” you said, crawling over him, straddling him between your legs. He sat up obediently, his hands removing your bra with ease before settling on the waistband of your underwear. He tried to get you to sit up without asking so he could pull them down but you shook your head.

“Move your legs sweetheart,” he said, finding you shake your head again. You leaned forward and kissed him harshly, pulling his bottom lip out between your teeth. “But I like this pair,” he whined, not wanting to rip the material off of your body.

“No one said you had to do that,” you mumbled along his jaw, dipping your lips to suck against the sensitive skin, leaving a mark hard enough to bruise. Dean inhaled sharply as your lips latched onto the same spot, sucking again.

“Just remember you wanted rough,” he said, his hands lifting you off of him long enough to yank down your underwear. Yours found his boxers and snapped the elastic on his hips, making him shudder.

“You are not in charge,” you said, pushing on his chest so he fell backwards, his chest already heaving at the promise. “You do what I say, figure out what I want without me having to say it, and you’ll get your record broken in no time, Frat Boy,” you said, grinding your hips against his growing cock, still trapped away.

He grunted in response but nodded his head anyways, fisting his hands in the sheets. His eyes fluttered shut as he relaxed into the fluid motion of you against him, slowly building him up. When his face was content, his hips shifting for a harder angle but not doing anything more, you reached a hand down to slip into his boxers. You wrapped your hand around his erection, pumping his shaft before sliding your thumb over his slit, watching his body thrust up for more.

“Fuck, Y/N,” said Dean, his voice strained at the sudden change in tempo. You gave a small smile as you let him snap his hips as he pleased, tightening your grip to give more friction for him until he was suddenly coming, surprising the both of you. “Shit,” he said, one of his hands coming to rest on his head.

“Stay put,” you said, rolling off the bed to grab a towel and clean him up, pulling his boxers off of his shaky legs. Dean’s face was tinted red as you realized he was embarrassed at coming so quickly. “Baby,” you said, running your hand over his chest to interlace with the one in his hair.

“What,” he said, a trickle of coldness in his words. You gave him a soft kiss as you reached your hand to his hip, trying to roll him on top of you.

“Make me feel good,” you said, his green eyes warm again. Dean took his turn to trap you between his legs, his hand dipping down to tease you as you lay back and enjoy it like Dean had done. After ten or so minutes, you were getting close and you knew Dean would be ready for more. 

“What?” he said with a smirk as you glanced down. He was already hard, the reprieve more than enough time for him. You shoved his shoulder lightly and Dean fell back against the bed, waiting for your next command.

“Make yourself feel good,” you said, moving off the bed to sit at Dean’s desk chair. He gave you a curious look but moved his hand down regardless. He so hardly ever let you watch him, mostly because he was always concerned with making sure you were getting as much pleasure as possible. 

Watching Dean rub himself off was something you were enjoying almost as much as him. You tried to focus on the spots he touched the most, the way he liked to touch himself so you could touch him in those same ways. 

“My face is up here sweetheart,” he said with such cockiness you blushed. Your eyes met his just in time to see them glaze over with bliss as Dean groaned, coming again. Dean was nearly panting as his head dropped, going lax as you pushed him down onto the bed. “Let me stay down this time. I don’t think I can get up again.”

“You let me do all the work,” you said, slipping his semi-hard cock through your folds, a strangled sound escaping Dean. You ground and rocked on him with ease, feeling the jolts of his pulse run through his cock as he grew hard quickly.

“You’re trying to kill me,” he half-whined, half-growled, his hands practically ripping the sheets he was holding on so tight.

“Never,” you said coyly, lifting up you hips and slamming down, a yelp escaping Dean. He was sensitive and you could tell the rougher pace was verging on too much but his eyes were begging for more. This time when he came, it was a silent cry, almost sending you over the edge yourself but you weren’t done yet.

“You gotta…” Dean muttered, his hands on your hips, slipping you off of him.

“Calm down, Dean,” you whispered, running your hands over his body. You stayed like that with him for a good long while, running over his edges and lines, appreciating him as he let himself come down and ready for more. 

“I’m good,” he said eventually, a hand moving to get you back on top of him. He was probably aware even in his haze that you hadn’t come yet and would want to return the favor.

“How do you want it?” you asked when he was fully sheathed inside you, simply resting for the moment.

“Fast,” he said, your eyebrows raising and Dean’s hands on your hips lifting you up and down, pulling a moan from you. “Unless you can’t handle it,” he said with a sexy smirk.

“Anything for you,” you said, not holding back, letting yourself set the rhythm, Dean falling in line for a short while until his thrusts faltered, desperately holding off for you. “Go ahead, come for me, Dean.”

With that, Dean let go, sending you into an orgasm that almost rivaled the one Dean was experiencing. You shakily came down from yours to find Dean wrecked, already fighting off the urge to pass out and sleep off his weariness.

“Was that good?” you asked, Dean putting his thumb up as he breathed heavy and slow. “Need anything?”

One of his hands tickled your skin, all the energy he could muster, and you curled him up next to you. You were sure when you awoke, Dean would be in the big spoon position like always, but you did enjoy the rare occasion he let you hold him.

 

The next morning you felt Dean’s arm over your waist, his soft snores on the back of your neck. You nuzzled back onto him, ready to fall back into slumber when his lips pressed against your skin. There was a smile in them he wanted you to feel.

“I can’t wait,” he mumbled, his hold on you keeping you from turning to face him.

“For what, Dean?” you asked, knowing you’d never get a straight answer out of him.

“You’ll see,” he said. “You’ll see real soon.”


	20. Chapter 20

**Summary for the Chapter:**

> Dean and reader have a night neither will ever forget…

It was a chilly November night as you and Dean walked from the frat to your apartment. In the morning you’d grab Sam and head to the cabin for Thanksgiving break. You were looking forward to seeing the Winchesters all together again. 

“Sweetheart?” you heard Dean say beside you. You blinked as you turned to look up at him. His face was soft as he gave you a smile. “What are you thinking about?”

“Just glad to be a part of the Winchester’s lives,” you said, stepping around a puddle that Dean had to resist jumping in. 

“They’re glad to have you too. I may have heard that one of them, not to name names or anything, may be hopelessly in love with you,” he said, giving your hand a squeeze.

“Is it the cute one?” you said with a coy smile. Dean pretended to look around before nodding. 

“Super cute,” he said with a wink. You hummed as you came to your block, Dean’s urge to not kick a pile of leaves on the corner too strong as he scattered them around the sidewalk.

“Do you think I have a shot with him?” you asked, Dean starting to chuckle.

“Hopelessly in love babe. I think you could look at him and he’d be yours forever. Not that I’m speaking from experience,” said Dean.

“You think I should make a move on our little Sammy at Thanksgiving?” you said, slipping out on Dean’s hand and cocking an eyebrow. You gave him a devilish grin and shrugged as Dean shook his head.

“You little…you’re lucky I’m in a good mood tonight or else I’d have to punish you,” he said, wrapping an arm around your waist, holding you tight.

“You’re always in a good mood around me….and you know I like to get in trouble with you,” you said, giving him a wink.

“You make me happy. I got something I want to do tonight anyways,” he said, turning the two of you up the steps to your apartment.

“What’s that?” you asked, looking up to Dean. He gave a little smile as he opened the front door and brought you both inside.

“Show you how much I love you,” he said, taking no time at all to lock up before his hands were on you.

Dean could barely contain himself as you got off your boots and coat, throwing your flannel off and the tank top underneath by the time you’d unzipped his jacket. It wasn’t the urgency that showed he wanted fast and hard tonight though. He needed you, badly, as if he were starving for it.

A heap of clothes lay in your entrance as Dean picked you up, lips crashing into yours as he walked to your bedroom. He threw the covers back before setting you down and covering the two of you up again. You hadn’t quite seen him like this before. One second you thought he might want to draw this out and tease, the next he was rubbing his hard cock against your clit, giving you time to get wet and ready for him.

“Dean,” you moaned, holding onto the back of his head before he distracted you with a long, drawn out kiss. It was almost as if he needed you to know something he wasn’t ready to share yet. One of your hands trailed down his back and gave a little push, telling him you wanted more.

Dean obliged by pushing inside with one smooth motion. You could feel yourself clench around him, feel his familiar throbbing that quaked through your very core. You moved your hips and could feel his groan through your chest, making you want to do it again and again. Dean let you set a moderate pace, falling in line with what you wanted, seeming as if he were more concerned with how to kiss you as if it were your first time.

Your orgasm was sudden and you weren’t prepared for it but Dean was right there with you, coming within a few more quick thrusts. You always came right along with one another, never wanting the other to feel left out. Your hips slowed and stopped as Dean’s fingers graced over your skin as if he’d never touched that before either. When he was soft, he pulled out with a content look on his face, telling you to take a shower first as he had something he needed to do.

When you were out of the bathroom, Dean had already put fresh sheets on the bed, the dirty ones in the washer. He washed up quickly while you collected your clothes from the front of the house and made sure everything was ready to go in the morning. 

“Ready for bed?” you asked, sensing Dean was perhaps in a rush because of your early drive in the morning. He ran a hand through his hair, pushing the short strands up in a way that made you smile ridiculously. He was so handsome it almost hurt.

“No, I uh, wanted to ask you something,” he said, shoving his hands into the pockets of his pajama pants, rocking on his heels excitedly.

“Go for it,” you said, standing up, running a hand along his arm. He looked like he wanted to blush but fought it back as best he could.

“Want to make a bet?” he asked, a little smirk crossing his cheeks. You shook your head as you laughed.

“With you? Sure,” you said, grinning like an idiot at the man in front of you. It was okay though, he was smiling like one too.

“Say yes,” he said, taking a step forward, putting his body close to yours. He was still able to send that rush of excitement down your spine at having him nearby.

“Yes,” you said, looking up through your lashes. “So what bet did I just lose?” you asked, knowing you’d never get tired of this game. Dean only wrapped his arms around you and kissed you on the lips gently.

“We both won this time,” he said, looking down with his brilliant green eyes. 

“What’d I win?” you asked, leaning up on your tip toes, tangling your arms behind his neck to pull him down.

“Me,” he said, his lips whispering against yours. 

“You just…” you said, realizing what Dean had actually asked you, what he said he’d ask you one year ago. He never looked scared of your answer though and you were so glad he already knew how you felt. “One forever with Dean Winchester, coming right up,” you said, moving your lips closer to kiss his.

“Is that a yes? You know what I meant?” he asked, the heat from him spilling over you. “Y/N, I love you and I want you to be by my side. I-”

“Yes, Dean. It’s always been a yes. Now kiss your fiancé,” you said, a perfect sense of calm that was always with you when you were with him filling you. His kiss was slow, probably the slowest of your lives but also the most important thus far. This was permanent now. If there had been any fears left with either of you, they were gone for good with that kiss.

When you pulled back, you could feel your cheeks hurting from smiling so hard, could feel how your arms had wrapped around Dean in a tight embrace. His held you close as you memorized this one perfect moment in your life. You’d fallen for your frat boy and he for his sweetheart, and never regretted one wonderful second of it. You rested your head against his chest as he nestled his atop yours, holding onto what was always each others.

“Mine,” you both whispered, to yourselves and one another. “Always mine.”


	21. Two Years Timestamp

**Summary for the Chapter:**

> Dean has a surprise for reader as they start to think of life after grad school…

“Dean,” you mumbled, shoving on his arm. He grumbled and tightened his hold on you. “Dean! You have to let me out of this bed!”

“Uh, no I don’t,” murmured Dean, smiling against the back of your neck. “Morning, sweetheart.”

“Frat boy, I have class in an hour,” you said, knowing well enough that you weren’t leaving unless he let you. “If I don’t get in the shower in the next five minutes-”

“You have to turn in your midterm project, sweetheart, no need to get all dressed up. You can throw on a pair of sweats and my shirt and we get to stay in bed another half hour,” he said, nuzzling the back of your head. “I’ll stay right here while you’re gone and then you can just come to back to bed.”

“Did you honestly forget you have your-”

“Oh shit,” said Dean, scrambling up and out of bed, rushing over to the closet and picking through his clothes, spinning around like a madman. “Fuck, I already had to cancel once because of class. He’s going to be pissed at me if I do it again.”

“First off, it’s Sam. Second, why don’t you tell me what you two are up to?” you asked. Dean smiled but shook his head, pulling on yesterday’s jeans, fumbling with his belt. “You know you aren’t allowed to do wedding stuff without me.”

“It’s not wedding stuff. Just…stuff. A surprise. You love surprises from me,” he said, grabbing a shirt from the floor, quickly dropping it when he remembered he’d cleaned up last night using that. “Washcloth. Next time washcloth.”

“Your surprises are typically  _not_  things I would want Sammy around for,” you said, stretching as you got out of the warm bed and padded over to the closet. Dean nodded but kept his mouth shut, silently teased you with a smug grin. “You know what would be a good surprise? A dog.”

“No! We barely can handle planning a wedding. We eat takeout half the week. A living creature is not something we are capable of caring for,” he said. You scoffed and he crossed his arms. “Do you remember the goldfish?”

“You mean the goldfish you won at the carnival and was half dead by the time we got home? That one?” you asked, Dean pursing his lips.

“We aren’t getting a dog,” he said. You pouted and he rolled his eyes. “When we get an actual house-”

“This is a house,” you said with a big grin.

“This is a tiny ass one bedroom house that barely fits all our stuff. Not to mention it doesn’t even have a driveway for Baby,” he said, resting his hands on your hips. “We haven’t even decided where we want to live yet.”

“Well Sam accepted that job near your parents place after he graduates and Bobby wants to hand over the business to you,  _which you’d be perfect for_ , and I will find something around there. I want live near where you grew up Dean,” you said. Dean shook his head and you sighed.

“You’re getting your masters for a reason, Y/N. You didn’t spend all that money and work that hard to work at Starbucks,” he said, resting his forehead on yours. “Where ever  _you_  get a job, we’ll go.”

“I want to be near my family,” you said, moving his hands off you, tired of having this conversation over and over with him. “I got to shower.”

You heard him come in once he heard the curtain shut and the water come on, quietly brushing his teeth and probably grabbing your brush to fix his hair.

“Are we having a fight?” he asked. You tilted your head back and got a face full of water, cursing under your breath as you wiped it away.

“No, Dean,” you said softly, poking your head out, Dean’s concern about being late for Sam replaced with his guilty face. “I just…”

“I bookmarked a few jobs I saw last night near here at a research place. You’d make a lot, even starting out. But it’s far from home so I didn’t bring it up but…it’s your life, your decision,” he said. He put on a smile when you frowned.

“It’s  _our_  life,” you said, his face softening. “Dean, we could live in a cardboard box and I wouldn’t care. Money is important but it’s not the purpose of living. You, my family, that’s what I want, baby. We have to sleep in your childhood bedroom, I got to work at Bobby’s…alright then. I’m game. I want to go home. If you don’t, that’s okay and we’ll figure out where to go but I love you way more than I ever will some job, even a dream one.”

“I did a dumb again,” he said, running his hand on the back of his neck. He shrugged and grinned.

“No, no dumbo here,” you said. “A caring dork? Yes, for sure. No dumb though.”

“You know I’ve spent two years wondering why you said yes. Who knew being a complete and utter fool was the way to stealing your heart,” he said.

“A complete and utter fool that is about to blow off Sam again,” you said, Dean’s eyes wide as he spun around and booked it out of there, shouting an ‘I love you’ at you as the front door was slammed shut. “Frat boy, what am I ever going to do with you…”

 

“Y/N,” said Dean, smiling when you heard him come inside the house a few hours later. “I got a surprise.”

“I made you a pie,” you said, pointing into the kitchen, Dean’s brain distracted long enough for you to grab the bag out of his hands, peaking your head inside. “Did you buy flavored lube?”

“Yeah,” he said as you gave it back. “No, that isn’t your surprise either.”

“I would hope not,” you said, stopping in your tracks. “Was  _Sam_ with you when you bought this?”

“Hey, I saw him buying some too. I think Ruby’s got a little streak in her like yourself,” said Dean. 

“You think Sam and Ruby are up to what we were back then?” you asked, Dean grimacing for a moment. “What flavor did he get?”

“Vanilla. I’m pretty sure Sam’s got some learning to do on the sex front,” said Dean, a laugh pulling itself from you as you grabbed a plate for him. “What?”

“This coming from the guy who’s virginity I took,” you said, Dean scowling at you, throwing his arms over your shoulders while you cut him a large slice. “I was your first everything, Frat boy.”

“Oh, we got kinky pretty quickly,”  said Dean, nipping at your jaw. “Still are.”

“Yes, chocolate flavored lube. You’re an absolute  _mad man_ ,” you teased, Dean biting at your neck playfully until you were spinning around to give him his pie.

“I did enjoy that time with the chocolate syrup at the cabin,” said Dean, raising an eyebrow. “Which is part of your surprise. We’re going up tomorrow for the long weekend.”

“Alright. Sam riding with us or-”

“No, Sam. Just us,” said Dean. You leaned against the counter and gave him a smirk. 

“Well then you should have bought more lube,” you said, Dean rolling his eyes.

“I don’t need it, I get you wet like that. It’ll be fun. We haven’t been in a couple of months,” said Dean.

“No arguments from me.”

 

“I didn’t realize your parents were coming over,” you said, spotting their car in the driveway. You climbed out and grabbed a bag from the trunk, Dean getting his own out but staying quiet. You had a feeling of what he was up to but not until you were inside exchanging hugs with your soon to be in-laws did it hit you. “You bought the cabin, didn’t you?”

“Do you have any idea how hard it is to surprise you?” asked Dean, sighing but still wearing a smile. “Yes, I did.”

“Dean mentioned over the summer you guys were thinking of coming back to the area once you both graduate. We don’t really need both houses now that the boys are grown up,” said John. “Plus now we get to visit and don’t have to clean anything!”

“It’s not official  _yet_ ,” said Dean. You wandered around the kitchen island, looking over everything as you felt the gaze of all three Winchesters on you. “I wasn’t going to buy a house without you.”

“Oh course at a family discount,” said Mary. “There’s no problems with it. You get the shed with the kayaks, the diving dock, furniture too if you want.”

“Everything will stay in my parents names until we have jobs. It’s a good size house and we can update things here and there as we go if you want but I know you love it so I figured it’d be a great place to start this part of our lives,” said Dean.

“I want to put up a fence,” you said, looking out the back window. “Not yet or even a huge one but you know when we have kids so they don’t wander in the lake back there.”

“We did the same thing when the boys were little,” said Mary. “Then we took it down when they got older.”

“We can have a fence. A dog like we talked about too,” said Dean with a grin.

“What was the secret stuff with Sam about?” you asked, Dean blushing and rubbing the back of his neck.

“The cabin was supposed to go to both of the boys. Dean wanted to be sure Sam was alright with you two taking it,” said John. 

“I told him he’s allowed to visit as much as he wants,” said Dean. “Not that I thought you’d mind.”

“No, I want Sammy to come over just as much as he does now. The apartments he was looking at for next year are only a fifteen minute drive,” you said. You walked over to the back door and looked outside at the changing leaves, remembering how nearly three years ago that backyard was where you thought you were a simple bet to Dean. You remembered his promise that he was telling the truth and that walk that night and the way the stars looked when you lay in your tent realizing how wrong you were.

“Y/N,” said Dean, suddenly by your side and enveloping your hand in his. “If you don’t want to live here, we don’t have to. It’s completely your choice.”

“You told me you loved me here. It’s perfect to start a family,” you said. You felt Dean nod back over his shoulder, rocking back and forth on his heels. “Do your parents want to stay for lunch?”

“I’m sure they’d love to but they’ve got a date apparently,” said Dean. You turned around and saw Dean’s parents talking quietly, both laughing at something and closing their mouths when they caught your staring. “We’re taking the house guys.”

“We figured as much,” said John. “We’ve got to run for our reservation but we’ll see you two at our place for lunch tomorrow?”

“Yeah, yeah, go have fun on your old people date,” said Dean, shoving them out.

“I still got some moves,” said John. “Dean got it from somewhere you know.”

“Dad! Leave! Now!” said Dean, closing the door after his parents scurried out. “Jeez, I’m glad we only have to deal with the one set.”

“I’m pretty sure my parents with yours would have been the death of us,” you said, looking around with a big smile. “I think they would have liked how my life ended up. A home and a big family that loves me.”

“They’d be proud of you,” said Dean, pulling you into a tight embrace. “I am, sweetheart.”

“Yeah, but you’re  _supposed_  to be proud of me,” you said, Dean blushing again. “You like me or something Winchester?”

“I’ve kind of got this major crush on you,” he said, taking both your hands in his and swinging them lightly. “I’m sort of deeply in love with you and your sass.”

“My sass?” you teased, Dean cocking his head.

“Your sass…that ass,” said Dean, bending down and picking you up. “I think a home welcoming is in order.”

“Did you bring the chocolate?” you asked, Dean humming. “Let me freshen up and then you can have a taste.”

“Yes mam.”

 

“Fuck, Y/N,” said Dean with a pant, almost giggling as he collapsed on the bed next to you. “You and that throat of yours is going to send me to an early grave.”

“Did you say something? My brain is mush after not one but  _two_ orgasms in the span of twenty seconds. I don’t think I can walk straight anymore,” you said, Dean spinning his body around and pulling your body in close. “Good ole 69. Never fails.”

“Damn right it doesn’t,” he said, laughing to himself. “I can’t wait to marry you.”

“Less than two months away, Frat boy. I’m so glad I went to that party. I didn’t even  _want_  to since I figured some drunk frat guy would hit on me and I’d have to turn him down,” you said.

“I had like two shots before I got up the nerve to talk to you, that was it,” said Dean. “You in skinny jeans is intimidating, sweetheart.”

“You in a black tee is intimidating,” you said.

“Oh, so me every single day then?” said Dean, flashing you a smile.

“Ah, shut up,” you said, burrowing your head into his chest. “Love you.”

“Love you too sweetheart,” he said with a hug. “Honestly, do you want to live here?”

“Yeah, it’s always felt like this magical place to me, our private paradise. I can’t wait to have that all the time,” you said.

“How about after graduation and we settle down into our jobs and into the house, we get a dog next summer? Something big and tough to take care of you if I’m not around,” said Dean.

“Or we could get a little cute adorable fluff ball,” you said, Dean pursing his lips.

“Or we could get both,” he said, your eyes lighting up. “Good practice for a few years from now.”

“Perfect,” you said, kissing his nose. “A tiny ball of cuteness and a big ball of cuteness.”

“I thought I said tough,” said Dean, your head shaking.

“No, you said something big and fluffy,” you said, Dean wearing a smirk.

“I’m pretty sure I said big and tough, little missy,” said Dean. 

“Big fluffy things can be tough and protective too,” you said.

“Oh really?” he asked.

“You are,” you said, Dean rolling his eyes. “You really are though!”

“Yeah, yeah,” he said, kissing your cheek. “Come on, we got to clean up. We have a hot date in an hour.”

“Wait, is today…” you asked, Dean smiling to himself. “Three years since we met, isn’t it.”

“Yup. So wash up, put on that backless little black dress of yours and prepare yourself for the best night of your life,” he said. 

“Best night of my life? That’s a tall order,” you said, Dean raising an eyebrow.

“Want to bet on it?” he asked.

“With you? You’re on.”


	22. The Night They Met Timestamp

**Summary for the Chapter:**

> Part one of Frat Boy from Dean’s POV

If someone had told Dean he would be meeting you that night in October, he wouldn’t have in a million years acted like the stereotype you were probably expecting.

He was simply cutting through the kitchen, again annoyed that no one ever closed the back door after grabbing something from the coolers on the porch. He was midway to closing it when he caught you walking to the cooler, back to him.

You were in the simplest outfit in the world. A pair of faded jeans and a black flowy tank top that somehow was magically hugging all the right spots on you. Dean had seen a hundred other girls tonight, some in the exact same outfit but something about you made him want to stick around. 

Until he realized he had about two seconds before you stood back up and caught him staring. 

He figured go for broke and own it, whistling at you, watching you give it right back before you had to go and spin around.

He barely managed to recover with a witty comeback. He’d had girlfriends before. He’d been around plenty of pretty girls. They were nothing compared to the way you smirked as you slid past him, returning to the party. Dean wandered outside to collect himself, mind instantly filling with a million questions.

Were you here with friends? A boyfriend? What kind of beer were you drinking? Did you even like that kind of beer or were you drinking it because it was there? Were you enjoying yourself? Did you like to dance? Or did you like to hang out instead? Were you a center of attention at these kinds of things? Or did you stick to the edges, wandering around? Did you-

“Dean,” said Sam slapping him on the back, snapping him out of the laps his mind was running. “What the hell is going on with you? You look like you’re trying to figure out life’s greatest mystery or something.”

“I met a girl,” said Dean. “Well…we flirted for two seconds before she went back inside.”

“So you were trying to figure out life’s greatest mystery then,” said Sam, laughing when Dean gave him a glare. “Go find her. Say hey. Tell her you’re not as much of a loser as I’m sure she thinks you are.”

“Sam, I acted like a total frat guy,” said Dean, Sam rolling his eyes. “Like super bad. She thinks I’m a douche.”

“Maybe she’s into douche’s,” said Sam with a shrug.

“But that’s not me,” said Dean, sighing as he stared at the door.

“You won’t know unless you go find her,” said Sam. “Who was this chick? I’ve never seen you fall head over heels like this.”

“I’m not head over heels,” said Dean, Sam sipping on his beer. “I’m just…she felt…ah, fuck. I’m in over my head on this one.”

“Maybe she’s the one. Go find her dumbass,” said Sam, patting Dean’s back.

Dean grumbled as he went back inside, nearly an hour going by before he saw you ducking into the first floor bathroom. He waited outside, thinking that was more than weird and tried to backtrack into the living room and catch you in there but you flung open the door too fast, looking him up and down.

You were looking at him like he was someone completely different, that he was a guy that could show you a good time. He saw you lick your lips without realizing, nodding your head that you saw something you liked. 

Damn it, why’d he never get past first base? Why did he even  _want_ to go past it with you, a complete stranger? Sure, he was a sucker, a sap, a hopeless romantic that Sammy liked to tease him for. But Dean was forgetting all that as he looked you over. It was the completely wrong way to go about this, about saying hi and we should be friends first and find out what we have in common and he should definitely take you to dinner before we start this part.

The message never got to his mouth, going with the cocky option again, watching you seem to eat it up and shoving him further down the hole until Dean was wide eyed in the pool room, more in shock than you were over the bet the two of you had made.

He almost wanted to lose just so you wouldn’t find out how much of a fool he was for being all talk.

Finally,  _finally_  common sense hit him when he realized he’d won and you were going to keep you word.

“You do want this right?” he asked by the stairs, pulling you in close. Never in a million years would he want you to go through with this unless he absolutely knew you wanted to. 

Your hand tugging on his belt with a mischeiouvs smirk, eyes glancing up the stairs wondering what the hell was taking so long made him swell up with something, that feeling he’d always shoved down in front of any other being.

He was sweating bullets by the time you were in his room but thankfully it was dark and you were more focused on teasing him than noticing him wince his face for the briefest moment. 

He didn’t know what to do other than to start with a kiss, quickly making it rough to hide the nerves. You were eating it up and Dean had heard plenty of times that building up to the main event made it better.

Two hours later Dean was saying goodnight to you, waving as you got in a cab he called, shaking his head at the night he’d had. 

“Did I see you dancing, Dean?” teased Sam, throwing his arm over Dean’s shoulders. “With a girl.  _A cute girl_.”

“Yeah,” said Dean, sporting a huge smile as Sam looked him up and down, going wide eyed. “What?”

“Nothing,” said Sam, not asking the question Dean saw swimming around in his head and thankful he knew better. “You get her number?”

“Of course I…” said Dean, patting his pocket, remembering he’d left his phone in his room. “Shit.”

“I’m sure you’ll run into her again. School’s only got like…eight thousand students…” said Sam, Dean wincing. “Sorry.”

“No, you’re right. I’ll probably see her on the quad or something. I hope.”

 

Tuesday afternoon Dean was grinning like an idiot. You were sitting on a bench near the edge of the quad just like Sam had said, head in a notebook, looking over something intently from the looks of it. His feet carried him over before he figured out what he wanted to say, going back to that cocky charade that he knew was safe with you.

Still, when you called him Frat Boy a part of him found it endearing, like somehow you knew it was a joke too. Another party invite was easy and he could actually pull you aside and talk to you this time, get to know you and maybe do this the right way.

Until you brought up the idea of a bet that intrigued and scared the hell out of him. He knew he got lucky with you not finding out before but he was going to embarrass himself like crazy if he agreed to this. Then again, that wouldn’t be such a bad thing. Not if he wanted to really know you.

Dean didn’t even realize he’d said yes until you were standing up with a smirk, looking him up and down like maybe you were a bit nervous too.

What the hell had he gotten himself into?


End file.
